기본 정보
- 표준 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- 분자식
- C21H30O3
- 평균 분자량
- 330.5 g/mol
개요
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.
이름 및 식별자
- 우선 이름
- 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
- 현지명
- 하이드록시프로제스테론
- 영어명
- 17α-Hydroxyprogesterone
- 분자식
- C21H30O3
- 분자량
- 330.46
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- 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
물성
구조 계산 물성
- XLogP
- 3.2
- 극성 표면적
- 54.4 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 3
- 회전 가능 결합 수
- 1
- 무거운 원자 수
- 24
- 형식 전하
- 0
- 복잡도
- 635
실험 및 물리화학적 성질
Melting Point
222-223 °C
219 - 220 °C
Collision Cross Section
184.4 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID6040747]
183.4 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
187.57 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]
179.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
202.46 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
187 Ų [M-H]-
물리화학적 성질
- 녹는점
- 276 °C · 276°C
- 끓는 점
- 407.89 °C · 407.89°C (rough estimate)
- 밀도
- 1.0998 · 1.0998 (rough estimate)
- 굴절률
- 90 ° · 90 ° (C=1, CHCl3)
- 인화점
- 9 ℃ · 9℃
- 저장 조건
- Sealed in dry,Room Temperature
- 용해도
- 클로로포름에 용해됨
- 물리적 상태
- Solid
- 산도 계수 (pKa)
- 13.03 · 13.03±0.60(Predicted)
- 색상
- 흰색에서 거의 흰색
- 수용성
- 5.056 mg/L · 5.056mg/L(20℃)
- Merck
- 14 · 14,4839
- BRN
- 3218109 · 3218109
- 주요 응용
- 소분자 약용
- NIST
- -4 · Pregn-4-ene-3,20-dione, 17-hydroxy-(68-96-2)
화학적 성질
White Solid
안전 및 규제
GHS 분류
GHS Classification
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.
유해성 정보
Regulatory Information
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.
독성 정보
Human Toxicity Excerpts
...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.
Non-Human Toxicity Excerpts
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/
안전 데이터
- wgk
- 3
- rtecs
- TU5060000
- ridadr
- UN1230 - class 3 - PG 2 - Methanol, solution
- HS 번호
- 38220090
- risk_code
- 61-39/23/24/25-23/24/25-11
- hazard_code
- T,F
- safety_code
- 53-22-36/37/39-45-36/37-16
- 유해 물질 데이터
- 68-96-2(Hazardous Substances Data)
화학 및 산업
약리 정보
ATC Code
G - Genito urinary system and sex hormones
QG - Genito urinary system and sex hormones
Mechanism of Action
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.
FDA Pharmacological Classification
21807M87J2
HYDROXYPROGESTERONE
Chemical Structure [CS] - Progesterone Congeners
Established Pharmacologic Class [EPC] - Progestin
Hydroxyprogesterone is a Progestin.
Absorption, Distribution and Excretion
...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/
용도 및 제조
Uses
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
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).
General Manufacturing Information
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/
응용 분야
용도Progesteron. It was isolated from adrenal glands.
상·하류 제품 정보
상류 원료
하류 제품
공급사50 곳
추가 설명
정의ChEBI: A 17alpha-hydroxy steroid that is the 17alpha-hydroxy derivative of progesterone.
관련 반응
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