Hydroxyprogesteron

17-Hydroxyprogesterone

HCID 6238CAS 110850-01-6

Grundinformationen

Standard-SMILES
CC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C
InChIKey
DBPWSSGDRRHUNT-CEGNMAFCSA-N
Summenformel
C21H30O3
Durchschnittliche Molmasse
330,5 g/mol

Überblick

17alpha-hydroxyprogesterone is a 17alpha-hydroxy steroid that is the 17alpha-hydroxy derivative of progesterone. It has a role as a metabolite, a progestin, a mouse metabolite and a human metabolite. It is a 17alpha-hydroxy-C21-steroid, a tertiary alpha-hydroxy ketone and a 17alpha-hydroxy steroid. It is functionally related to a progesterone.

Namen und Bezeichner

Bevorzugter Name
17-Hydroxyprogesterone
IUPAC
(8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
Lokaler Name
Hydroxyprogesteron
Englischer Name
17α-Hydroxyprogesterone
Summenformel
C21H30O3
Molmasse
330.46

Namen und Synonyme

hydroxyprogesterone68-96-217ALPHA-HYDROXYPROGESTERONE17-HydroxyprogesteroneProdixProdoxGestageno gador17-alpha-Hydroxyprogesterone17-Hydroxypregn-4-ene-3,20-dioneGestagenoHidroxiprogesteronaHydroxyprogesteronum
Weitere Namen anzeigen
17A-HYDROXYPROGESTERONE17α-Hydroxyprogesterone17-OHPHYDROXYPROGESTERONE, 17A-U 3096
17alpha-Hydroxy-4-pregnene-3,20-dione17-OH Progesteronedelta(4)-Pregnene-17alpha-ol-3,20-dione17alpha-Hydroxy-progesteronePregn-4-ene-3,20-dione-17-olIdrossiprogesteronealpha Hydroxy progesteroneDTXSID6040747

Datenbank-Bezeichner

CAS
110850-01-6、68-96-2
PubChem CID
6238
DTXSID
DTXSID00859075
ChEMBL
CHEMBL1062
ChEBI
CHEBI:17252
UNII
21807M87J2
EC Number
200-699-4
Nikkaji
J4.862C

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,2
Polarare Oberfläche (TPSA)
54,4 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
1
Schwere Atome
24

Experimentelle und physikochemische Eigenschaften

LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]
SpringerMaterials PropertiesChemical shift
LogP3.17
Color/FormRHOMBIC OR HEXAGONAL LEAFLETS FROM ACETONE OR ALCOHOL
Solubility0.00648 mg/mL
Animal DrugsPharmaceuticals -> Animal Drugs -> Approved in Taiwan

Physikochemische Eigenschaften

Schmelzpunkt
276 °C · 276°C
Siedepunkt
407.89 °C · 407.89°C (rough estimate)
Dichte
1.0998 · 1.0998 (rough estimate)
Brechungsindex
90 ° · 90 ° (C=1, CHCl3)
Flammpunkt
9 ℃ · 9℃
storage temp.
Sealed in dry,Room Temperature

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H360 (95.1%): May damage fertility or the unborn child [Danger Reproductive toxicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Regulatory Information · 2 Einträge

Status: Active Update: 28-07-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/20280

Hydroxyprogesterone: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Other Safety InformationIMAP assessments - Pregn-4-ene-3,20-dione, 17-hydroxy-: Environment tier I assessment
Hazard Classes and CategoriesRepr. 1B (95.1%)

Toxikologische Informationen

Interactions...ESTROGEN ENHANCED SUPPRESSIVE EFFECT OF PROGESTIN & LED TO GENERAL USE OF MIXTURE OF TWO. /PROGESTINS/
Human Toxicity Excerpts · 5 Einträge

...MAY CAUSE EDEMA & LOCAL REACTIONS @ SITE OF INJECTION.

MOST COMMON EFFECTS ARE NAUSEA, EDEMA, & IRREGULAR VAGINAL BLEEDING. OTHER REPORTED EFFECTS INCL WT GAIN, DECR LIBIDO, DEPRESSION, JAUNDICE, & CONGESTIVE HEART FAILURE. /CAPROATE/

...HYDROXYPROGESTERONE CAPROATE OCCASIONALLY CAUSES HYPERSENSITIVITY, COUGHING, OR DYSPNEA. IN RARE INSTANCES IT MAY CAUSE VIRILIZATION OF FEMALE FETUS. /CAPROATE/

CONTINUOUS ADMIN OF PROGESTIN IN SUFFICIENT DOSE ABOLISHES CYCLE FOR AS LONG AS IT IS GIVEN & LEADS TO OVARIAN & ENDOMETRIAL ATROPHY. VERY SMALL DOSES MAY ALTER STRUCTURE OF ENDOMETRIUM & CONSISTENCY OF CERVICAL MUCUS WITHOUT DISRUPTING CYCLE OR INHIBITING OVULATION. /PROGESTINS/

For more Human Toxicity Excerpts (Complete) data for 17ALPHA-HYDROXYPROGESTERONE (10 total), please visit the HSDB record page.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Non-Human Toxicity Excerpts · 2 Einträge

NO VIRILIZING EFFECTS WERE OBSERVED IN DBA MICE GIVEN DAILY SC INJECTIONS OF 0.25 MG 17ALPHA-HYDROXYPROGESTERONE CAPROATE ON DAYS 16-19 OF GESTATION OR IN SPRAGUE-DAWLEY RATS GIVEN 5 MG DAILY FROM DAY 14-19 OF GESTATION. /CAPROATE/

OF 19 YOUNG, RANDOM-BRED FEMALE RABBITS INJECTED IM WITH 13 MG...IN SESAME OIL ON ALTERNATE WK FOR UP TO 109 WK, 14 DEVELOPED...CYSTS OF ENDOMETRIUM DURING 1ST 267 DAYS. IN 7/8 ANIMALS...ALIVE @ 109 WK, CYSTS WERE UNILOCULAR... IN CONTROL...FEW CYSTS...LESS THAN 0.3 MM IN DIAM...SMALL NON-NEOPLASTIC POLYPS... /CAPROATE/

Sicherheitsdaten

wgk
3
ridadr
UN1230 - class 3 - PG 2 - Methanol, solution
hs_code
38220090
RTECS-Nr.
TU5060000
risk_code
61-39/23/24/25-23/24/25-11
hazard_code
T,F

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

G - Genito urinary system and sex hormones

QG - Genito urinary system and sex hormones

Mechanism of Action · 2 Einträge

ADMIN OF ESTROGEN & PROGESTIN, AS CONTAINED IN COMBINATION OR SEQUENTIAL PREPN, COULD INTERFERE WITH FERTILITY IN ANY ONE OF SEVERAL WAYS. HOWEVER, IT IS CLEAR THAT, AS CURRENTLY USED, MIXTURE INHIBITS OVULATION. ...CONTINUED ACTION OF PROGESTERONE SERVES TO INHIBIT RELEASE OF LH. /PROGESTINS/

IT ACTS AS ANTIGONADOTROPHIC AGENT ON ANTERIOR PITUITARY INHIBITING FSH RELEASE &, THUS, FOLLICULAR GROWTH, ESTROGEN PRODUCTION, & ESTRUS. IT ALSO INHIBITS LH RELEASE, THUS PREVENTING OVULATION, CORPORA LUTEA FORMATION, & FURTHER PROGESTERONE SECRETION. BY INHIBITING LH...HOLDS PROGESTERONE LEVELS IN CHECK.

Metabolism/Metabolites17alpha-hydroxy-progesterone has known human metabolites that include 17Beta-21-dihydroxyprogesterone.
FDA Pharmacological Classification · 5 Einträge

21807M87J2

HYDROXYPROGESTERONE

Chemical Structure [CS] - Progesterone Congeners

Established Pharmacologic Class [EPC] - Progestin

Hydroxyprogesterone is a Progestin.

Absorption, Distribution and Excretion · 3 Einträge

...DURATION OF ACTION IS LONGER /THAN PROGESTERONE/, BUT ITS ONSET OF ACTION IS SLOWER. SINGLE INJECTION OF SOLN OF HYDROXYPROGESTERONE CAPROATE IN OIL WILL EXERT PROGESTATIONAL EFFECTS FOR 1-2 WK. /CAPROATE/

ABOUT 50-60% OF ADMIN RADIOACTIVE PROGESTERONE APPEARS IN URINE & ABOUT 10% IN FECES. ... WHEN PROGESTERONE IS GIVEN FOR PROLONGED PERIOD, DURING LUTEAL PHASE OF CYCLE, OR DURING PREGNANCY, LARGER PROPORTION (25-30%) APPEARS IN URINE AS PREGUANEDIOL. /PROGESTERONE/

RATE OF TURNOVER OF ENDOGENOUS PROGESTERONE IS UNUSUALLY RAPID, T/2 IN BLOOD BEING FEW MIN, & DOUBTLESS EXOGENOUS MATERIAL IS HANDLED IN SAME WAY. SMALL AMT...IS STORED IN BODY FAT... PRESUMABLY, ABSORPTION FROM INTESTINAL TRACT IS PROMPT, BUT COMPD IS RAPIDLY TRANSFORMED DURING PASSAGE THROUGH LIVER... /PROGESTERONE/

Tissue LocationsAdipose Tissue

Verwendung und Herstellung

Uses · 4 Einträge

MEDICATION (VET)

MEDICATION

Use (kg; approx.) in Germany (2009): >25

This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

Methods of Manufacturing · 2 Einträge

HYDROXYPROGESTERONE IS ESTERIFIED BY HEATING WITH CAPROIC ANHYDRIDE IN PRESENCE OF P-TOLUENE-SULFONIC ACID UNDER ATMOSPHERE OF NITROGEN. US PATENT 2,753,360. /CAPROATE/

JULIAN ET AL, US PATENT 2,648,662 (1953 TO GLIDDEN)...STORK ET AL, US PATENTS 2,802,839 & 2,805,203 (BOTH 1957 TO SYNTEX)...DULANEY, MCALEER; US PATENTS 2,777,843; 2,786,856/7; 2,813,060 (ALL 1957 TO MERCK & CO)...PEDERSON, US PATENT 3,000,883 (1961 TO UPJOHN).

Formulations/PreparationsHYDROXYPROGESTERONE CAPROATE INJECTION, USP (DELALUTIN), IS PROVIDED AS OILY SOLN OF 125 MG/ML (IN SESAME OIL) OR 250 MG/ML (IN CASTOR OIL) FOR IM INJECTION. /CAPROATE/
Use ClassificationPharmaceuticals -> Animal Drugs -> Approved in Taiwan
General Manufacturing Information · 1 Eintrag

PROGESTINS CANNOT BE EQUATED AS GROUP WITH PROGESTERONE BECAUSE SOME ARE INHERENTLY ESTROGENIC, SOME SLIGHTLY ANDROGENIC, & SOME PURELY PROGESTATIONAL; CORRESPONDINGLY, THEIR OVULATION-INHIBITING POTENTIALITIES MAY BE MEDIATED IN SOMEWHAT DIFFERENT WAYS. /PROGESTINS/

Anwendungen

VerwendenProgesteron. It was isolated from adrenal glands.

Anbieter50 Anbieter

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shanghai Biolang Biotechnology Co., Ltd.+86-15970428662 +86-13397199602 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: A 17alpha-hydroxy steroid that is the 17alpha-hydroxy derivative of progesterone.

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