17-Hydroxyprogesterone

330.46

330.46

200-699-4

21807M87J2

15468

DTXSID6040747

C87242

RHOMBIC OR HEXAGONAL LEAFLETS FROM ACETONE OR ALCOHOL

G - Genito urinary system and sex hormones

38220090

54.4

3.2

Solid

1.0998 (rough estimate)

222-223 °C

482.9ºC at 760 mmHg

9℃

90 ° (C=1, CHCl3)

5.056mg/L(20 ºC)

-20°C Freezer

SPECIFIC OPTICAL ROTATION (CHLOROFORM, 1.0417%): +105.6 DEG @ 17 °C/D

183.4 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|183.75 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|179.9 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|187 Ų [M-H]-

ODORLESS OR HAS SLIGHT ODOR /CAPROATE/|WITH SLOW HEATING UNDERGOES MOLECULAR REARRANGEMENT ACCOMPANIED BY PARTIAL RESOLIDIFICATION & BECOMES MOLTEN @ 276 °C|CRYSTALS FROM CHLOROFORM + METHANOL /ACETATE/|WHITE CRYSTALLINE SOLID /ACETATE/|For more Other Experimental Properties (Complete) data for 17ALPHA-HYDROXYPROGESTERONE (7 total), please visit the HSDB record page.

UN1230 - class 3 - PG 2 - Methanol, solution

3

61-39/23/24/25-23/24/25-11

53-22-36/37/39-45-36/37-16

TU5060000

T,F

CRYSTALS SHOULD NOT BE EXPOSED TO HEAT & LIGHT /CAPROATE/

P201, P202, P281, P308+P313, P405, P501

H360

|Danger|H360 (92.86%): May damage fertility or the unborn child [Danger Reproductive toxicity]|P201, P202, P281, P308+P313, P405, and P501|Aggregated GHS information provided by 42 companies from 4 notifications to the ECHA C&L Inventory.

Cyproterone has been associated with serum enzyme elevations during therapy in 10% to 14% of patients, but these elevations are usually transient and mild and often resolve even without dose modification. More importantly, cyproterone has been associated with many instances of clinically apparent liver injury with jaundice. The time to onset has ranged from a few months to as long as a year, but typically arises within 3 to 6 months of starting treatment. The liver injury is almost always hepatocellular with moderate to marked elevations in serum aminotransferase levels and minimal increases in alkaline phosphatase. Mixed and more cholestatic injury occurs occasionally and may have a more favorable prognosis. Importantly, the hepatocellular injury associated with cyproterone use is often severe and the mortality rate of patients presenting with jaundice is at least 10% (these patients frequently being elderly men with advanced prostate cancer and not qualifying for emergency liver transplantation). Immunoallergic features (fever, rash, eosinophilia) are uncommon, as are autoantibodies. Some patients, however, appear to respond to corticosteroid therapy and rare instances of autoimmune-hepatitis like injury have been attributed to cyproterone. Improvement is usually seen within 1 to 2 weeks of stopping cyproterone and resolution within 1 to 3 months. Nevertheless, many examples of progressive liver injury leading to death from hepatic failure despite prompt discontinuation of therapy have been reported. In rare cases, recovery has been incomplete and patients have had residual evidence of chronic liver disease or cirrhosis.

...ESTROGEN ENHANCED SUPPRESSIVE EFFECT OF PROGESTIN & LED TO GENERAL USE OF MIXTURE OF TWO. /PROGESTINS/

Cyproterone is a steroidal antiandrogen that has been used in the treatment of prostate cancer in many countries of the world, but not in the United States. Cyproterone therapy can be associated with serum enzyme elevations during therapy and has been linked to many instances of clinically apparent acute liver injury, some of which were fatal.

Antineoplastic Agents

THERAPEUTIC USES. ...CONTRACEPTION...FUNCTIONAL UTERINE BLEEDING... DYSMENORRHEA...PREMENSTRUAL TENSION...ENDOMETRIOSIS...THREATENED & HABITUAL ABORTION...EVALUATION OF OVARIAN FUNCTION & DIAGNOSIS OF PREGNANCY...SUPPRESSION OF POST-PARTUM LACTATION...ENDOMETRIAL CARCINOMA. /PROGESTINS/|CHEMOTHERAPEUTIC AGENTS USEFUL IN NEOPLASTIC DISEASE: HYDROXYPROGESTERONE CAPROATE (DELALUTIN) FOR ENDOMETRIUM, RENAL CELL, BREAST, PROSTATE. /CAPROATE/|...IN METASTATIC & RECURRENT ENDOMETRIAL CARCINOMA. THEY PRODUCE REMISSIONS FOR PROLONGED PERIODS IN ABOUT 25% OF PT WHEN METASTASES ARE CONFINED TO PULMONARY AREA. LARGER DOSES...WHEN DISEASE RECURS IN OSSEOUS, INTRA-ABDOMINAL, OR PELVIC SITES. ...USED PARENTERALLY IN RENAL CARCINOMA. /PROGESTAGEUS/|WHEN USED TO REGULATE IRREGULAR ESTRUS CYCLE, IT IS USUALLY COMBINED WITH ESTROGEN. /CAPROATE/|For more Therapeutic Uses (Complete) data for 17ALPHA-HYDROXYPROGESTERONE (15 total), please visit the HSDB record page.

VET: AVOID BREEDING TREATED ANIMALS UNTIL SECOND POST-TREATMENT ESTRUS CYCLE. SEVERE PYOMETRA-LIKE SYNDROMES HAVE OCCURRED IN TREATED ANIMALS DEPRIVED OF NORMAL ESTRUS STIMULATING EFFECTS ON UTERINE ENDOMETRIUM...|WHETHER TAKING ORAL CONTRACEPTIVES OF PROGESTIN-ESTROGEN TYPE PRODUCED HIGHER INCIDENCE OF OCULAR & OPHTHALMO-NEUROLOGIC DISEASES THAN WOULD OCCUR SPONTANEOUSLY IN UNMEDICATED WOMEN OR IN PREGNANT WOMEN WAS NOT ANSWERED CONCLUSIVELY... /PROGESTINS/|CONTRAINDICATIONS TO THEIR USE ARE THROMBOEMBOLIC DISORDERS OR PAST HISTORY OF THESE CONDITIONS, MARKEDLY IMPAIRED HEPATIC FUNCTION, KNOWN OR SUSPECTED CARCINOMA OF BREAST OR OTHER ESTROGEN-DEPENDENT NEOPLASIA, & UNDIAGNOSED GENITAL BLEEDING. /ORAL CONTRACEPTIVES/

...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/

17alpha-hydroxy-progesterone has known human metabolites that include 17Beta-21-dihydroxyprogesterone.

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.

...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.

17 alpha Hydroxyprogesterone

HYDROXYPROGESTERONE 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/

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/

Lipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]|Pharmaceuticals -> Animal Drugs -> Approved in Taiwan