Levonorgestrel

Modify Date: 2024-01-02 11:00:39

Levonorgestrel Structure
Levonorgestrel structure
 Common Name Levonorgestrel
CAS Number 797-63-7 Molecular Weight 312.446
Density 1.1±0.1 g/cm3 Boiling Point 459.1±45.0 °C at 760 mmHg
Molecular Formula C21H28O2 Melting Point 206ºC
MSDS Chinese USA Flash Point 195.4±21.3 °C
Symbol GHS07 GHS08
GHS07, GHS08		 Signal Word Danger

 Use of Levonorgestrel


Levonorgestrel is a synthetic progestogen used as an active ingredient in some hormonal contraceptives.Target: Progesterone ReceptorA synthetic progestational hormone with actions similar to those of progesterone and about twice as potent as its racemic or (+-)-isomer (norgestrel). It is used for contraception, control of menstrual disorders, and treatment of endometriosis. It is usually supplied in a racemic mixture (Norgestrel, 6533-00-2). Only the levonorgestrel isomer is active. Levonorgestrel is marketed mostly as a combination oral contraceptive under several brand names such as Alesse, Triphasil, and Min-Ovral [1].

 Names

Name [18,19-Dinorpregn-4-en-20-yn-3-one-13-ethyl-17-hydroxy-,(17.α.)-(-)-]
Synonym More Synonyms

 Levonorgestrel Biological Activity

Description Levonorgestrel is a synthetic progestogen used as an active ingredient in some hormonal contraceptives.Target: Progesterone ReceptorA synthetic progestational hormone with actions similar to those of progesterone and about twice as potent as its racemic or (+-)-isomer (norgestrel). It is used for contraception, control of menstrual disorders, and treatment of endometriosis. It is usually supplied in a racemic mixture (Norgestrel, 6533-00-2). Only the levonorgestrel isomer is active. Levonorgestrel is marketed mostly as a combination oral contraceptive under several brand names such as Alesse, Triphasil, and Min-Ovral [1].
Related Catalog
References

[1]. Gallos, I.D., et al., Oral progestogens vs levonorgestrel-releasing intrauterine system for endometrial hyperplasia: a systematic review and metaanalysis. Am J Obstet Gynecol, 2010. 203(6): p. 547 e1-10.

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Boiling Point 459.1±45.0 °C at 760 mmHg
Melting Point 206ºC
Molecular Formula C21H28O2
Molecular Weight 312.446
Flash Point 195.4±21.3 °C
Exact Mass 312.208923
PSA 37.30000
LogP 3.92
Vapour Pressure 0.0±2.6 mmHg at 25°C
Index of Refraction 1.571
Storage condition 2-8°C

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
JF8225000
CHEMICAL NAME :
18,19-Dinor-17-alpha-pregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-, (+)-
CAS REGISTRY NUMBER :
797-63-7
LAST UPDATED :
199612
DATA ITEMS CITED :
21
MOLECULAR FORMULA :
C21-H28-O2
MOLECULAR WEIGHT :
312.49
WISWESSER LINE NOTATION :
L E5 B666 OV MUTJ E2 FQ F1UU1 -D

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1820 mg/kg/26W-I
TOXIC EFFECTS :
Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Biochemical - Metabolism (Intermediary) - other proteins
REFERENCE :
PHARAT Pharmazie. (VEB Verlag Volk und Gesundheit, Neue Gruenstr. 18, Berlin DDR-1020, Ger. Dem. Rep.) V.1- 1946- Volume(issue)/page/year: 34,319,1979 ** TUMORIGENIC DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
29 mg/kg/69W-C
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Skin and Appendages - tumors
REFERENCE :
CRSBAW Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. (SPPIF, B.P.22, F-41353 Vineuil, France) V.1- 1849- Volume(issue)/page/year: 168,1190,1974 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
274 ug/kg
SEX/DURATION :
female 52 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - menstrual cycle changes or disorders
REFERENCE :
FESTAS Fertility and Sterility. (American Fertility Soc., 608 13th Ave. S, Birmingham, AL 35282) V.1- 1950- Volume(issue)/page/year: 24,191,1973
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
20 ug/kg
SEX/DURATION :
female 1 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
REFERENCE :
INJFA3 International Journal of Fertility. (Allen Press, 1041 New Hampshire, St., Lawrence, KS 66044) V.1- 1955- Volume(issue)/page/year: 20,156,1975
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
109 ug/kg
SEX/DURATION :
female 26 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
REFERENCE :
INJFA3 International Journal of Fertility. (Allen Press, 1041 New Hampshire, St., Lawrence, KS 66044) V.1- 1955- Volume(issue)/page/year: 17,17,1972
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
5 ug/kg
SEX/DURATION :
female 1 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
REFERENCE :
CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 7,367,1973
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
8 ug/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - menstrual cycle changes or disorders
REFERENCE :
CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 11,31,1975
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Implant
DOSE :
38160 ng/kg
SEX/DURATION :
female 22 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - menstrual cycle changes or disorders Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
REFERENCE :
CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 18,411,1978
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Implant
DOSE :
1600 ug/kg
SEX/DURATION :
female 52 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
REFERENCE :
CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 12,615,1975
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
10 ug/kg
SEX/DURATION :
female 6 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
REFERENCE :
IJEBA6 Indian Journal of Experimental Biology. (Publications & Information Directorate, CSIR, Hillside Rd., New Delhi 110 012, India) V.1- 1963- Volume(issue)/page/year: 11,321,1973
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
960 mg/kg
SEX/DURATION :
female 2 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
REFERENCE :
CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 16,541,1977
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
10 ug/kg
SEX/DURATION :
female 6 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - uterus, cervix, vagina
REFERENCE :
IJEBA6 Indian Journal of Experimental Biology. (Publications & Information Directorate, CSIR, Hillside Rd., New Delhi 110 012, India) V.1- 1963- Volume(issue)/page/year: 17,684,1979
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
120 ug/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 35,459,1985
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1600 ug/kg
SEX/DURATION :
female 5 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - uterus, cervix, vagina
REFERENCE :
CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 12,529,1975
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1800 ug/kg
SEX/DURATION :
female 43 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - ovaries, fallopian tubes
REFERENCE :
CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 16,499,1977
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
4500 ug/kg
SEX/DURATION :
female 3 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
REFERENCE :
CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 21,61,1980
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1875 ug/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
REFERENCE :
CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 30,153,1984
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
300 ug/kg
SEX/DURATION :
female 2 day(s) pre-mating 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)
REFERENCE :
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: 117,167,1973 *** REVIEWS *** IARC Cancer Review:Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 21,479,1979 IARC Cancer Review:Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 21,479,1979 TOXICOLOGY REVIEW CMROCX Current Medical Research and Opinion. (Clayton-Wray Pub. Ltd., 1a High St., Alton, Hants., UK) V.1- 1972- Volume(issue)/page/year: 4,309,1976

 Safety Information

Symbol GHS07 GHS08
GHS07, GHS08
Signal Word Danger
Hazard Statements H312 + H332-H351-H360
Precautionary Statements P201-P261-P280-P308 + P313
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xn:Harmful
Risk Phrases R20/21/22;R40
Safety Phrases S22-S36
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS JF8225000
HS Code 2937290090

 Synthetic Route

 Customs

HS Code 2937290090

 Articles81

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 Synonyms

(8R,9S,10R,13S,14S,17R)-13-Ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one
Mirena
postinor
13-Ethyl-17-ethynyl-17b-hydroxy-4-gonen-3-one
17a-Ethynyl-18-homo-19-nortestosterone
L-Norgestrel
Norgeston
(8S,9R,10S,13R,14R,17S)-13-Ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one
13b-Ethyl-17a-ethynyl-17b-hydroxygon-4-en-3-one
Levonorgestrel
18-METHYLNORETHINDRONE
[3H]-Levonorgestrel
18-Methyl-17a-ethynyl-19-nortestosterone
(−)-Norgestrel
Norplant
(17a)-13-Ethyl-17-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one
Levonelle
13-β-ETHYL-17-α-ETHYNYL-17-β-HYDROXYGON-4-EN-3-ONE
follistrel
17b-Hydroxy-18-methyl-19-nor-17a-pregn-4-en-20-yn-3-one
microluton
(8R,9S,10R,13S,14S,17R)-17-Ethinyl-13-ethyl-17-hydroxy-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-on
Levonova
(8R,9S,10R,13S,14S,17R)-13-éthyl-17-éthynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tétradécahydro-3H-cyclopenta[a]phénanthrén-3-one
17a-Ethynyl-18-methyl-19-nortestosterone
EINECS 212-349-8
17a-Ethynyl-17-hydroxy-18-methylestr-4-en-3-one
D-Norgestrel
Microval
dextronorgestrel
NORGESTREL, (+)-
Norgestrel (+)-form
MFCD06198806
13-Ethyl-17-hydroxy-18,19-dinor-17a-pregn-4-en-20-yn-3-one
Norgestrel
17a-Ethynyl-13-ethyl-19-nortestosterone
Microlut
UNII:3J8Q1747Z2
norplant2
D(−)-Norgestrel
NorLevo
wy-5104
(17a)-(-)-13-Ethyl-17-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one
D-(-)-Norgestrel
(-)-Norgestrel
13-Ethyl-17a-ethynyl-17-hydroxygon-4-en-3-one
(8a,9b,10a,13a,14b)-13-Ethyl-17-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one
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