Betamethasone

Pharmaceuticals -> Steroids

Pharmaceuticals -> Dermatologicals -> Corticosteroids, dermatological preparations

Pharmaceuticals -> Listed in ZINC15

log Kow= 1.94

1.1

Crystals from ethyl acetate

WHITE, CRYSTALLINE POWDER

SOLUBILITIES: 1 G IN 1.6 ML WATER & 6.25 ML METHANOL; PRACTICALLY INSOL IN ACETONE, CHLOROFORM /SODIUM PHOSPHATE/

SPARINGLY SOL IN ACETONE AND ALC

SPARINGLY SOL IN DIOXANE, METHANOL; VERY SLIGHTLY SOL IN CHLOROFORM & ETHER

In water, 66.5 mg/l @ 25 °C

5.05e-02 g/L

Breast Feeding; Lactation; Milk, Human; Corticosteroids, Topical; Glucocorticoids; Anti-Inflammatory Agents

Breast Feeding; Lactation; Milk, Human; Corticosteroids, Systemic; Glucocorticoids; Anti-Inflammatory Agents

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Dermatological medicines > Anti-inflammatory and antipruritic medicines

Pharmaceuticals -> UK Veterinary Medicines Directorate List

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

178°C

231-234 °C, decomposes

231 - 234 °C

Danger

H330 (51%): Fatal if inhaled [Danger Acute toxicity, inhalation]

P203, P260, P264, P270, P271, P273, P280, P284, P304+P340, P316, P318, P319, P320, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 102 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Status: Active Update: 20-12-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/13677

Betamethasone: Does not have an individual approval but may be used under an appropriate group standard

The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl betamethasone acetate,betamethasone sodium phosphate, betamethasone dipropionate, and betamethasone valerate approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Betamethasone acetate,betamethasone sodium phosphate, betamethasone dipropionate, and betamethasone valerate/

Betamethasone acetate and betamethasone disodium phosphate aqueous suspension. ... It is used or intended for use by intra-articular injection of horses for the treatment of various inflammatory joint conditions; for example, acute and traumatic lameness involving the carpel and fetlock joints. ... Not for use in horses intended for food. For use only by or on the order of a licensed veterinarian. /Betamethasone acetate/

Betamethasone dipropionate and betamethasone sodium phosphate aqueous suspension. ... Conditions of use -- (1) Dogs. (i) It is used as an aid in the control of pruritus associated with dermatoses. ... (2) Horses. (i) It is used as an aid in the control of inflammation associated with various arthropathies. ... Not for use in horses intended for food. ... Restrictions. Federal law restricts this drug to use by or on the order of a licensed veterinarian. /Betamethasone dipropionate, Betamethasone sodium phosphate/

Gentamicin sulfate, betamethasone valerate otic solution. ... Conditions of use. (1) The drug is used or indicated for use in dogs in the treatment of acute and chronic otitis externa caused by bacteria sensitive to gentamicin; the drug is also used or indicated for use in dogs and cats in the treatment of superficial infected lesions caused by bacteria sensitive to gentamicin. ... For use by or on the order of a licensed veterinarian. /Betamethasone valerate/

For more FDA Requirements (Complete) data for BETAMETHASONE (8 total), please visit the HSDB record page.

Jager-Roman E et al; Dev Pharmacol Ther 5: 127-35 (1982). Increased theophylline metabolism in premature infants after prenatal betamethasone administration.

Coggiola F et al; Minerva Ginecol 34 (3): 191-4 (1982). Three cases of acute pulmonary edema in pregnant women treated with tocolytics and betamethasone.

Mehta AC et al; Br J Pharm Pract 3: 10-14 (1982). Betamethasone 17-valerate: investigation into its stability in betnovate after dilution with emulsifying ointment: quantitation of degradation products. /Betamethasone 17-valerate/

Kubota K, et al; J Pharm Sci 82: 450-6 (1993). Percutaneous absorption: single layer model using betamethasone valerate suspension.

For more Special Reports (Complete) data for BETAMETHASONE (9 total), please visit the HSDB record page.

Betamethasone tablets should be stored in well-closed containers at 2-30 °C. Betamethasone oral soln should be protected from light and stored in well-closed containers at a temp <40 °C, preferably between 15 and 30 °C. Betamethasone sodium phosphate injection should be protected from light and stored at a temp <40 °C, preferably between 15 and 30 °C; freezing should be avoided. The sterile suspension containing betamethasone sodium phosphate and betamethasone acetate (Celestone, Soluspan) should be protected from light and stored at 2-25 °C; freezing should be avoided.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Hyperglycemic action of cortisone /betamethasone/ may offset hypoglycemic effect of chlorpropamide...

Induction of hepatic enzymes by corticosteroids may increase the formation of a hepatotoxic acetaminophen metabolite, thereby increasing the risk of hepatotoxicity, when they are used concurrently with chronic or high-dose acetaminophen therapy. /Corticosteroid/

Risk of gastrointestinal ulceration or hemorrhage may be increased when these substances /alcohol or nonsteroidal anti-inflammatory drugs (NSAIDs)/ are used concurrently with glucocorticoids; however, concurrent use of NSAIDs in the treatment of arthritis may provide additive therapeutic benefit and permit glucocorticoids dosage reduction. /Corticosteroids/

Concurrent use /of carbonic anhydrase inhibitors/ with corticosteroids may result in severe hypokalemia and should be undertaken with caution; serum potassium concentrations and cardiac function should be monitored during concurrent use. /Corticosteroids/

For more Interactions (Complete) data for BETAMETHASONE (25 total), please visit the HSDB record page.

/HUMAN EXPOSURE STUDIES/ A randomized study of the effects of betamethasone on maternal immune function and cellular resistance to infection was conducted in 86 pregnant women who received 12 mg im betamethasone at 28-32 wk gestation followed by a dose in 12 hr and then weekly until the completion of 32 wk gestation. Transient and incomplete suppression of the proliferative response to T-cell mitogen was demonstrated as early as 24 hr after drug admin. This suppression was noncumulative and short lived. No suppression of B-cell mitogen lipopolysaccharide was seen. Nonspecific cellular resistance to infection in betamethasone recipients showed incr phagocytic activity and normal bactericidal effects. It was concluded that specific and nonspecific immune function are intact in pregnant women after betamethasone admin.

/HUMAN EXPOSURE STUDIES/ Maternal immune suppression is a potentially significant adverse effect when betamethasone is used to hasten lung maturation of the fetus at risk for preterm delivery. However, incr incidence of infection has not been observed consistently after betamethasone treatment of pregnant women. This study was designed to determine if the cellular immune response to steroids may be modified during pregnancy in a way that would diminish the infection risk associated with steroid treatment. The effect of betamethasone on immunocytes among patients with preterm labor or in nonpregnant subjects were determined following admin of 12 mg of betamethasone im. ... The circulating leukocytes, lymphocytes, T-lymphocytes, and their subsets were serially measured/. Measurements were also made of localized leukocyte mobilization to serum filled skin chambers covering experimental inflammatory sites. Patients in preterm labor had increased WBC counts prior to treatment with betamethasone but no additional leukocytosis was induced nor was mobilization of leukocytes to the skin chambers decr. Lymphopenia and depression of T-cells was more transient among pregnant patients compared to nonpregnant. Thus, the pregnant patients studied had diminished or more transient potentially adverse immunocyte responses to betamethasone as compared to nonpregnant subjects.

/HUMAN EXPOSURE STUDIES/ The effects of corticosteroids, given for enhancement of fetal lung maturation, on fetal heart rate (FHR) are controversial and may decr its variability. FHR patterns were analyzed by computerized cardiotocography in 46 fetuses from 23 normal dichorionic twin pregnancies on days 0, 1, and 4-7 while the mothers received four im injections of 3 mg betamethasone sodium and 3 mg betamethasone acetate within 48 hr to enhance fetal lung maturation. Compared with pretreatment values, FHR showed a decr in long and short term variations; other parameters, e.g., the number of fetal movements, remained unchanged. However, decr FHR variation was followed by an incr in the acceleration rate after maternal admin of betamethasone. These modifications were transient and should not lead to unnecessary anxiety or intervention in otherwise normal fetuses.

/SIGNS AND SYMPTOMS/ The effects of gestational age (GA), body weight, and prenatal exposure to betamethasone and indomethacin on the glomerular filtration rate (GFR) on day 3 of life in preterm infants were studied. GFR measurements were performed in 147 preterm infants with a GA between 23.4 and 37.0 wk by means of the continuous inulin infusion technique. Mean GFR values incr significantly with GA (r = 0.60, p < 0.001) and with body weight (~r = 0.44, p <0.0011. Multivariate analysis indicated that GA was the most important determinant for this incr... Prenatal admin of betamethasone and indomethacin significantly (p< 0.001) incr the GFR in comparison with exposure to indomethacin alone to levels not different than those seen in patients who were not prenatally exposed to betamethasone or indomethacin. GFR were repeated in 40 preterm infants on day 10 after birth. During this 7 day period, a significant incr in GFR values (0.17 +/- 0.03 ml/min, p < 0.001) was detected. This postnatal incr in GFR values was independent of GA and was not influenced by prenatal exposure to betamethasone or indomethacin. /Data indicates that/ that prenatal exposure to betamethasone or indomethacin exerts significant effects on the renal function of preterm infants in the first days of life.

For more Human Toxicity Excerpts (Complete) data for BETAMETHASONE (6 total), please visit the HSDB record page.

/LABORATORY ANIMALS: Acute Exposure/ Large single doses of some steroids given parenterally to animals produce sedation, whereas others induce signs of central stimulation. To some extent these phenomena may be dose-related. /Corticosteroids/

/LABORATORY ANIMALS: Acute Exposure/ Single doses of glucocorticoids (0.5-8.0 g/kg) can suppress immune response in mice to extent that high mortality occurs as result of intercurrent infections over 1-3 wk. Rats are 10-20 times more sensitive than mice to this effect. /Corticosteroids/

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Conjunctival treatment of young pregnant New Zealand white rabbits with ophthalmic corticosteroids induced malformations. /Corticosteroids/

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ In order to elucidate the effects of corticosteroids on fetal hearts during midtrimester, pregnant rats were injected with a daily dose of betamethasone (1 mg/kg) from the 12th day through the 17th day of pregnancy. The fetal cardiovascular and pulmonary systems were studied on the 21st day of pregnancy (term). The treated fetuses showed the following signs of hydrops fetalis: retarded growth, pale, edematous skin, and decreased movement. The thymus and lung displayed prominent hypoplasia. The morphometry of the treated fetuses revealed: decr right ventricle mass by 37% and decr left ventricle mass by 29%... betamethasone had a significant effect on the developing fetal cardiovascular system, inducing hydrops fetalis. Additionally, betamethasone caused hypoplasia of the thymus and lung.

For more Non-Human Toxicity Excerpts (Complete) data for BETAMETHASONE (8 total), please visit the HSDB record page.

/SRP:/ Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

◉ Summary of Use during Lactation

◉ Summary of Use during Lactation

Betamethasone

Pharmaceutical

Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP

The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl betamethasone acetate,betamethasone sodium phosphate, betamethasone dipropionate, and betamethasone valerate approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Betamethasone acetate,betamethasone sodium phosphate, betamethasone dipropionate, and betamethasone valerate/

Betamethasone acetate and betamethasone disodium phosphate aqueous suspension. ... It is used or intended for use by intra-articular injection of horses for the treatment of various inflammatory joint conditions; for example, acute and traumatic lameness involving the carpel and fetlock joints. ... Not for use in horses intended for food. For use only by or on the order of a licensed veterinarian. /Betamethasone acetate/

Betamethasone dipropionate and betamethasone sodium phosphate aqueous suspension. ... Conditions of use -- (1) Dogs. (i) It is used as an aid in the control of pruritus associated with dermatoses. ... (2) Horses. (i) It is used as an aid in the control of inflammation associated with various arthropathies. ... Not for use in horses intended for food. ... Restrictions. Federal law restricts this drug to use by or on the order of a licensed veterinarian. /Betamethasone dipropionate, Betamethasone sodium phosphate/

Gentamicin sulfate, betamethasone valerate otic solution. ... Conditions of use. (1) The drug is used or indicated for use in dogs in the treatment of acute and chronic otitis externa caused by bacteria sensitive to gentamicin; the drug is also used or indicated for use in dogs and cats in the treatment of superficial infected lesions caused by bacteria sensitive to gentamicin. ... For use by or on the order of a licensed veterinarian. /Betamethasone valerate/

For more FDA Requirements (Complete) data for BETAMETHASONE (8 total), please visit the HSDB record page.

D07AC01

D - Dermatologicals

C - Cardiovascular system

S - Sensory organs

S - Sensory organs

D - Dermatologicals

Corticosteroids bind to the glucocorticoid receptor inhibiting pro-inflammatory signals, while promoting anti-inflammatory signals. Corticosteroids have a wide therapeutic window as patients may require doses that are multiples of what the body naturally produces. Patients who require long-term treatment with a corticosteroid should be counselled regarding the risk of hypothalamic-pituitary-adrenal axis suppression and increased susceptibility to infections.

Glucocorticoids inhibit neutrophil apoptosis and demargination, and inhibit NF-Kappa B and other inflammatory transcription factors. They also inhibit phospholipase A2, leading to decreased formation of arachidonic acid derivatives. In addition, glucocorticoids promote anti-inflammatory genes like interleukin-10. Corticosteroids like betamethasone can act through nongenomic and genomic pathways. The genomic pathway is slower and occurs when glucocorticoids activate glucocorticoid receptors and initiate downstream effects that promote transcription of anti-inflammatory genes including phosphoenolpyruvate carboxykinase (PEPCK), IL-1-receptor antagonist, and tyrosine amino transferase (TAT). On the other hand, the nongenomic pathway is able to elicit a quicker response by modulating T-cell, platelet and monocyte activity through the use of existing membrane-bound receptors and second messengers.

Corticosteroids interact with specific receptor proteins in target tissues to regulate the expression of corticosteroid responsive genes, thereby changing the levels and array of proteins synthesized by the various target tissues. As a consequence of the time required for changes in gene expression and protein synthesis, most effects of corticosteroids are not immediate, but become apparent after several hours. ... Although corticosteroids predominantly act to increase expression of target genes, there are well documented examples where glucocorticoids decrease transcription of target genes ... In contrast to these genomic effects, recent studies have raised the possibility that some actions of corticosteroids are immediate and are mediated by membrane-bound receptors. /Adrenocorticosteroids/

The mechanisms by which glucocorticoids inhibit glucose utilization in peripheral tissues are not fully understood. Glucocorticoids decrease glucose uptake in adipose tissue, skin, fibroblasts, thymocytes, and polymorphonuclear leukocytes; these effects are postulated to result from translocation of the glucose transporters from the plasma membrane to an intracellular location. These peripheral effects are associated with a number of catabolic actions, including atrophy of lymphoid tissue, decreased muscle mass, negative nitrogen balance, and thinning of the skin. /Adrenocorticalsteroids/

The mechanisms by which the glucocorticoids promote gluconeogenesis are not fully defined. Amino acids mobilized from a number of tissues in response to glucocorticoids reach the liver and provide substrate for the production of glucose and glycogen. In the liver, glucocorticoids induce the transcription of a number of enzymes involved in gluconeogenesis and amino acid metabolism, including phosphoenolpyruvate carboxykinase, glucose-6-phosphatase, and fructose-2,6-bisphosphatase. Analyses of the molecular basis for regulation of phosphoenolpyruvate carboxykinase gene expression have identified complex regulatory influences involving an interplay among glucocorticoids, insulin, glucagon, and catecholamine. The effects of these hormones and amines on phosphoenolpyruvate carboxykinase gene expression mirror the complex regulation of gluconeogenesis in the intact organism. /Adrenocorticalsteroids/

... /A/ major action of corticosteroids on the cardiovascular system is to enhance vascular reactivity to other vasoactive substances. Hypoadrenalism generally is associated with hypotension and reduced response to vasoconstrictors such as norepinephrine and angiotensin II. This diminished pressor response is explained partly by recent studies in experimental systems showing that glucocorticoids increase expression of adrenergic receptors in the vascular wall. Conversely, hypertension is seen in patients with excessive glucocorticoid secretion, occurring in most patients with Cushing's syndrome and in a subset of patients treated with synthetic glucocorticoids (even those lacking any significant mineralocorticoid action). /Adrenocorticosteroids/

For more Mechanism of Action (Complete) data for BETAMETHASONE (8 total), please visit the HSDB record page.

In a study that included Indian women of reproductive age, the half-life following a single intramuscular dose of betamethasone phosphate was 10.2 ± 2.5 hours.

The pharmacokinetics of betamethasone and its phosphate ester are described in 8 healthy adults after i.v. bolus injection of 10.6 mg betamethasone phosphate. Both compounds were measured by high-performance liquid chromatography with ultraviolet detection using sample handling methods which prevented hydrolysis of the ester in vitro. Betamethasone phosphate disappeared rapidly from plasma (mean half-life = 4.7 min) as betamethasone levels rose. Betamethasone plasma levels reached a peak 10-36 min after administration of the phosphate before declining in a biexponential manner. The terminal slow disposition phase had a mean half-life of 6.5 hr.

Serum half-life of betamethasone is about 3 hr.

The metabolism of betamethasone yields 6 metabolites. The metabolic processes include 6β hydroxylation, 11β-hydroxyl oxidation, and reduction of the C-20 carbonyl group followed by removal of the side chain.

All of the biologically active adrenocortical steroids and their synthetic congeners have a double bond in the 4,5 position and a ketone group at C 3. As a general rule, the metabolism of steroid hormones involves sequential additions of oxygen or hydrogen atoms, followed by conjugation to form water-soluble derivatives. Reduction of the 4,5 double bond occurs at both hepatic and extrahepatic sites, yielding inactive compounds. Subsequent reduction of the 3-ketone substituent to the 3-hydroxyl derivative, forming tetrahydrocortisol, occurs only in the liver. Most of these A ring-reduced steroids are conjugated through the 3-hydroxyl group with sulfate or glucuronide by enzymatic reactions that take place in the liver and, to a lesser extent, in the kidney. The resultant sulfate esters and glucuronides form water-soluble derivatives and are the predominant forms excreted in the urine. Neither biliary nor fecal excretion is of quantitative importance in human beings. /Adrenocortical Steroids/

9842X06Q6M

BETAMETHASONE

Established Pharmacologic Class [EPC] - Corticosteroid

Mechanisms of Action [MoA] - Corticosteroid Hormone Receptor Agonists

Betamethasone is a Corticosteroid. The mechanism of action of betamethasone is as a Corticosteroid Hormone Receptor Agonist.

Substances that reduce or suppress INFLAMMATION.

A group of CORTICOSTEROIDS that affect carbohydrate metabolism (GLUCONEOGENESIS, liver glycogen deposition, elevation of BLOOD SUGAR), inhibit ADRENOCORTICOTROPIC HORMONE secretion, and possess pronounced anti-inflammatory activity. They also play a role in fat and protein metabolism, maintenance of arterial blood pressure, alteration of the connective tissue response to injury, reduction in the number of circulating lymphocytes, and functioning of the central nervous system.

Drugs that are used to treat asthma.

The absorption and potency of any topical corticosteroid including betamethasone depends on the vehicle in which the steroid is delivered. For example, betamethasone dipropionate 0.05% ointment is classified as a highly potent topical steroid, while betamethasone dipropionate 0.05% cream or lotion is considered to be moderately potent. There are several structural modifications that can determine the potency of a topical corticosteroid. For example, corticosteroids containing a halogen at specific carbons, or that contain esters are more potent due to enhanced lipophilicity. As such, there is a marked difference between topical products containing betamethasone dipropionate vs. betamethasone valerate. Betamethasone dipropionate contains 2 esters which enhances its potency, while betamethasone valerate has only one ester and is less potent. It should be noted that the use of occlusive dressings with topical steroids significantly increases the absorption, increasing the risk for adverse effects.

Corticosteroids are eliminated predominantly in the urine.

In a study that included Indian women of reproductive age, the volume of distribution following a single intramuscular dose of betamethasone phosphate was 94,584±23,539 mL(s).

In a study that included Indian women of reproductive age, the CL/F following a single intramuscular dose of betamethasone phosphate was 6,466 ± 805 mL/hour.

Glucocorticoids ... absorbed systemically from sites of local administration, such as synovial spaces, the conjunctival sac, skin, and respiratory tract. When administration is prolonged, when the site of application is covered with an occlusive dressing, or when large areas of skin are involved, the absorption may be sufficient to cause systemic effects, including suppression of the HPA axis. /Adrenocorticalsteroids/

Following absorption, 90% or more of cortisol in plasma is reversibly bound to protein under normal circumstances. Only the fraction of corticosteroid that is unbound can enter cells to mediate corticosteroid effects. Two plasma proteins account for almost all of the steroid-binding capacity: corticosteroid-binding globulin (CBG; also called transcortin), and albumin. CBG is an alpha-globulin secreted by the liver that has high affinity for steroids but relatively low total binding capacity, whereas albumin, also produced by the liver, has low affinity but relatively large binding capacity. At normal or low concentrations of corticosteroids, most of the hormone is protein-bound. At higher steroid concentrations, the capacity of protein binding is exceeded, and a significantly greater fraction of the steroid exists in the free state. Corticosteroids compete with each other for binding sites on CBG. CBG has relatively high affinity for cortisol and most of its synthetic congeners and low affinity for aldosterone and glucuronide-conjugated steroid metabolites; thus, greater percentages of these latter steroids are found in the free form. /Adrenocortical Steroids/

MEDICATION (VET)

MEDICATION

Use (kg; approx.) in Germany (2009): >100

(1977) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1979) PROBABLY GREATER THAN 4.54X10+5 GRAMS

EXTRACTION OF HECOGENIN FROM AGAVE SISALANA (SISAL PLANT), THEN TRANSFER OF 12-OXO GROUP TO C-11, BROMINATION, TREATMENT WITH SODIUM HYDROXIDE, ACETYLATION, DEBROMINATION WITH ZINC DUST, AND REDUCTION WITH CALCIUM/LIQUID AMMONIA

Androstadienedione (multistep synthesis; coproduced with dexamethsone.

The 16-beta-methyl group is inserted into the appropriate precursor. The Merck method uses 3-alpha-acetoxy-16-pregnene-11,20-dione as the starting material. A 1,3-dipolar addition reaction with diazomethane at the double bond between positions 16 and 17...followed by alkaline cleavage or pyrolysis at ca. 200 °C then leads to the homologous 16-methyl-16-dehydro-20-keto compound. Stereospecific, catalytic hydrogentation of the double bond with palladium and calcium carbonate...the other essential groups and the dienone structure in ring A are then introduced in a series of steps to give betamethasone.

Available commercially as the alcohol and as the 17-valerate, 17-benzoate, 17,21-dipropionate, disodium 21-phosphate salt.

beta-Corlan, Becort, Betasolon, Betnelan, Celestene, Celestone, Dermabet, Diprolene, Visubeta

Celestovet /betamethasone acetate/

Bebate, Beben, Benisone, Euvaderm, Flurobate, Parbetan, Uticort /betamethasone benzoate/

For more Formulations/Preparations (Complete) data for BETAMETHASONE (7 total), please visit the HSDB record page.

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Pharmaceuticals -> Alimentary tract and metabolism -> Glucocorticoides