Betamethason

Betamethason · Betametasone · betamethasone standard · C22H29O5F · Dermabet · Celestone · 17,21-trihydr · FLUBENISOLONE

Identifikatoren & physikalische Daten

CAS No.	378-44-9
Summenformel	C22H29FO5
Durchschnittliche Molmasse	392,5 g/mol
Monoisotopische Masse	392,19990225 g/mol
SMILES	C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)CO
InChIKey	UREBDLICKHMUKA-DVTGEIKXSA-N
PubChem CID	9782
ChEMBL	CHEMBL632
ChEBI	CHEBI:3077
EC No.	206-825-4
DTXSID	DTXSID3022667
Lokaler Name	Betamethason

Chemische & physikalische Eigenschaften

XLogP	1,9
Polarare Oberfläche (TPSA)	94,8
H-Brücken-Donoren	3
H-Brücken-Akzeptoren	6
Frei drehbare Bindungen	2
Schwere Atome	28
Formalladung	0
Komplexität	805
Stoffklassen	Pharmaceutical
PFAS	PFAS -> Suspected persistent, mobile, toxic (PMT) PFAS or PFAS-like compounds
Arzneimittel	Pharmaceuticals -> SteroidsPharmaceuticals -> Dermatologicals -> Corticosteroids, dermatological preparationsPharmaceuticals -> Listed in ZINC15
LogP (Verteilungskoeffizient)	log Kow= 1.941.1
Geruch	ODORLESS
Color/Form	Crystals from ethyl acetateWHITE, CRYSTALLINE POWDER
Löslichkeit	SOLUBILITIES: 1 G IN 1.6 ML WATER & 6.25 ML METHANOLPRACTICALLY INSOL IN ACETONE, CHLOROFORM /SODIUM PHOSPHATE/SPARINGLY SOL IN ACETONE AND ALCSPARINGLY SOL IN DIOXANE, METHANOLVERY SLIGHTLY SOL IN CHLOROFORM & ETHERIn water, 66.5 mg/l @ 25 °C5.05e-02 g/LPractically insoluble in water, sparingly soluble in anhydrous ethanol, very slightly soluble in methylene chloride.58mg/L(25 ºC)
Human Drugs	Breast FeedingLactationMilk, HumanCorticosteroids, TopicalGlucocorticoidsAnti-Inflammatory AgentsCorticosteroids, SystemicFDA approved drugs -> Active ingredientDermatological medicines > Anti-inflammatory and antipruritic medicines
Animal Drugs	Pharmaceuticals -> UK Veterinary Medicines Directorate ListPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Endocrine Disruptors	Potential endocrine disrupting compound
Siedepunkt	568.2°C568.2±50.0 °C(Predicted)
Schmelzpunkt	178°C231-234 °C, decomposes231 - 234 °C235-237°C
Dichte	1.1283 (estimate)
Brechungsindex	118 ° (C=1, Dioxane)
Lagerbedingungen	0-6°C
pKa (Säurekonstante)	12.13±0.70(Predicted)
Aggregatzustand	Solid
Farbe	White to Off-White
Biologische Quelle	synthetic (organic)
Merck	14,1180
InChIKey	UREBDLICKHMUKA-DVTGEIKXSA-N
SMILES	[H][C@@]12C[C@H](C)[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]3(F)[C@@]2([H])CCC4=CC(=O)C=C[C@]34C
LogP (Verteilungskoeffizient)	2.01 at 25℃
CAS Datenbank	378-44-9(CAS DataBase Reference)
NIST chemische Informationen	Pregna-1,4-diene-3,20-dione, 9alpha-fluoro-11beta,17alpha,21-trihydroxy-16beta-methyl-(378-44-9)
EPA chemische Informationen	Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17,21-trihydroxy-16-methyl-, (11.beta.,16.beta.)- (378-44-9)

Sicherheit & Vorschriften

GHS-Einstufung	DangerH330 (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.
Regulatorische Informationen	Status: Active Update: 20-12-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/13677Betamethasone: Does not have an individual approval but may be used under an appropriate group standard
Weitere Sicherheitsinformationen	IMAP assessments - Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17,21-trihydroxy-16-methyl-, (11.beta.,16.beta.)-: Environment tier I assessment
FDA-Anforderungen	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 conditionsfor 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 gentamicinthe 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.
Special Reports	Jager-Roman E et alDev Pharmacol Ther 5: 127-35 (1982). Increased theophylline metabolism in premature infants after prenatal betamethasone administration.Coggiola F et alMinerva Ginecol 34 (3): 191-4 (1982). Three cases of acute pulmonary edema in pregnant women treated with tocolytics and betamethasone.Mehta AC et alBr 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 alJ 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.
Hazard Classes and Categories	Acute Tox. 2 (51%)
Lagerbedingungen	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 °Cfreezing 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 °Cfreezing should be avoided.
Entsorgungsverfahren	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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations.
Wechselwirkungen	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 glucocorticoidshowever, 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 cautionserum 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 Toxicity Excerpts	/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 variationsother 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.
Non-Human Toxicity Excerpts	/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.
Antidote and Emergency Treatment	/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/
Effects During Pregnancy and Lactation	◉ Summary of Use during Lactation
USGS Health-Based Screening Levels for Evaluating Water-Quality	BetamethasonePharmaceuticalSmith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP
Wassergefährdungsklasse (WGK)	2
Zollcode	29379000
RTECS-Nr.	TU4000000
R-Sätze (R)	40-48/20/21-61
Toxizität	LD50 oral in mouse: > 4500mg/kg
Gefahrensymbole	Xi,Xn,T
Sicherheitshinweise (S)	22-36-45-53
Lagerklasse	6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Gefahrstoffdaten	378-44-9(Hazardous Substances Data)
Gefahrenklasse	Repr. 1BSTOT RE 2

Anwendungen & Verwendung

Beschreibung

Shortly after the introduction of dexamethasone, betamethasone, which differs from dexamethasone only in configuration of the 16-methyl group, was made available for the treatment of rheumatic diseases and dermatologic disorders. This analogue, which contains a 16β-methyl group, has received sufficient clinical trial examination to indicate that it is as effective as dexamethasone or, perhaps, even slightly more active. Although this drug has been reported to be less toxic than other steroids, some clinical investigators suggest that it is best used for short-term therapy.

Verwenden

Betamethasone is a glucocorticoid used as an anti-inflammatory agent.