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Carboprost

Names

[ CAS No. ]:
35700-23-3

[ Name ]:
Carboprost

[Synonym ]:
prostin15m
Methyl-pgf2a
(15S)-15-Methylprostaglandin F2α
(E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-3-methyl-1-octenyl))cyclopentyl)-5-heptenoic acid
15s)-13e
15-Methyl-PGF2a
Prosta-5,13-dien-1-oic acid, 9,11,15-trihydroxy-15-methyl-, (5Z,9α,11α,13E,15S)-
15-ME-PGF2a
methyldinoprost
(5Z,9a,11a,13E,15S)-9,11,15-Trihydroxy-15-methylprosta-5,13-dien-1-oic Acid
(15S)-15-Methyl-PGF2a
Carboprost
(15S)-15-Methyl PGF2a
(15S)-15-Methylprostaglandin F2a
15-methyl-15S-PGF2α
(5Z,9α,11α,13E,15S)-9,11,15-Trihydroxy-15-methylprosta-5,13-dien-1-oic acid
MFCD00135249

Biological Activity

[Description]:

Carboprost (15(S)-15-Methyl Prostaglandin F2α) is a metabolically stable synthetic analog of prostaglandin F2α. Carboprost stimulates uterine contractions and induces abortion. Carboprost is used for postpartum hemorrhage due to uterine atony and for the termination of pregnancy in the second trimester[1][2].

[Related Catalog]:

Research Areas >> Endocrinology
Signaling Pathways >> Others >> Others

[In Vivo]

The methyl ester of Carboprost (15(S)-15-Methyl Prostaglandin F2α; 15M-PGF2 alpha, 12.5 mg/monkey) loweres serum progesterone to 12% of pretreatment values within 24 hours, however progesterone returnes to normal limits within 48 hours[1].

[References]

[1]. S J Carlan, et al. Effect of Intramuscular 15-methyl Prostaglandin F2 Alpha After Second-Trimester Delivery. Obstet Gynecol. 1997 Jan;89(1):5-9.

[2]. J W Wilks, et al. Inhibition of the Monkey Corpus Luteum With 15-methyl Prostaglandins. Prostaglandins. 1980 Nov;20(5):793-805.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
536.6±50.0 °C at 760 mmHg

[ Melting Point ]:
79-82ºC

[ Molecular Formula ]:
C21H36O5

[ Molecular Weight ]:
368.508

[ Flash Point ]:
292.4±26.6 °C

[ Exact Mass ]:
368.256287

[ PSA ]:
97.99000

[ LogP ]:
2.49

[ Vapour Pressure ]:
0.0±3.2 mmHg at 25°C

[ Index of Refraction ]:
1.565

[ Storage condition ]:
-20°C Freezer, Under Inert Atmosphere

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UK8021000
CHEMICAL NAME :
Prosta-5,13-dien-1-oic acid, 9,11,15-trihydroxy-15-methyl-, (5Z,9-alpha,11-alpha,13E,15S)-
CAS REGISTRY NUMBER :
35700-23-3
LAST UPDATED :
199612
DATA ITEMS CITED :
8
MOLECULAR FORMULA :
C21-H36-O5
MOLECULAR WEIGHT :
368.57

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
DOSE :
5 ug/kg
SEX/DURATION :
female 14 week(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - abortion
REFERENCE :
JOGBAS Journal of Obstetrics and Gynaecology of the British Commonwealth. (London, UK) V.68-81, 1961-74. For publisher information, see BJOGAS. Volume(issue)/page/year: 79,737,1972
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
DOSE :
12 ug/kg
SEX/DURATION :
female 30 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - abortion
REFERENCE :
PRGLBA Prostaglandins. (Geron-X, Inc., P.O. Box 1108, Los Altos, CA 94022) V.1- 1972- Volume(issue)/page/year: 14,785,1977
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraplacental
DOSE :
10 ug/kg
SEX/DURATION :
female 13 week(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - abortion
REFERENCE :
JOGBAS Journal of Obstetrics and Gynaecology of the British Commonwealth. (London, UK) V.68-81, 1961-74. For publisher information, see BJOGAS. Volume(issue)/page/year: 79,737,1972
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravaginal
DOSE :
60 ug/kg
SEX/DURATION :
female 42 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - abortion
REFERENCE :
CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 21,273,1980
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravaginal
DOSE :
10 ug/kg
SEX/DURATION :
female 15 week(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - abortion
REFERENCE :
JOGBAS Journal of Obstetrics and Gynaecology of the British Commonwealth. (London, UK) V.68-81, 1961-74. For publisher information, see BJOGAS. Volume(issue)/page/year: 79,737,1972
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
DOSE :
100 ug/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)
REFERENCE :
CYLPDN Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1980- Volume(issue)/page/year: 8,540,1987
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravaginal
DOSE :
500 ug/kg
SEX/DURATION :
female 1 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - other measures of fertility
REFERENCE :
PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 151,575,1976 *** REVIEWS *** TOXICOLOGY REVIEW AJOGAH American Journal of Obstetrics and Gynecology. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1920- Volume(issue)/page/year: 113,130,1972

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36:Irritating to the eyes.

[ Safety Phrases ]:
S26-S37/39

[ WGK Germany ]:
2

[ RTECS ]:
TU0175000

Precursor & DownStream

Precursor

DownStream

Related Compounds