Levonorgestrel

Modify Date: 2024-01-02 12:47:12

Levonorgestrel Structure
Levonorgestrel structure
 Common Name Levonorgestrel
CAS Number 6533-00-2 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 239-241ºC
MSDS N/A Flash Point 195.4±21.3 °C

 Use of Levonorgestrel


Norgestrel is a synthetic analog of progesterone, a compound commonly found in oral contraceptive pill, and a powerful neuroprotective antioxidant, preventing light-induced ROS in photoreceptor cells, and cell death[1][2].

 Names

Name levonorgestrel
Synonym More Synonyms

 Levonorgestrel Biological Activity

Description Norgestrel is a synthetic analog of progesterone, a compound commonly found in oral contraceptive pill, and a powerful neuroprotective antioxidant, preventing light-induced ROS in photoreceptor cells, and cell death[1][2].
Related Catalog
In Vitro Norgestrel (20 µM; 24 hours; 661W cells) treatment significantly increases cellular viability after serum deprivation and so it is demonstrated that Norgestrel is neuroprotective to stressed 661W cells[1]. Norgestrel (20 µM; 24 hours; 661W cells) treatment decreases apoptotic induced cleavage of PARP and caspase-3[1]. Norgestrel (20 µM; 6 hours; 661W cells) treatment bFGF is results in a significant upregulation of bFGF mRNA in photoreceptor cells[1]. Cell Viability Assay[1] Cell Line: 661W cells Concentration: 20 µM Incubation Time: 24 hours Result: Significantly increased cellular viability after serum deprivation. Western Blot Analysis[1] Cell Line: 661W cells Concentration: 20 µM Incubation Time: 24 hours Result: Decreased apoptotic induced cleavage of PARP and caspase-3. RT-PCR[1] Cell Line: 661W cells Concentration: 20 µM Incubation Time: 6 hours Result: A significant upregulation of bFGF mRNA over 1 hour.
In Vivo Norgestrel (100 mg/kg; intraperitoneal injection; for 6, 24 or 48 hours; Balb/c mice) treatment can prevent light-induced ROS in photoreceptor cells, and subsequent cell death. Norgestrel acts via post-translational modulation of the major antioxidant transcription factor Nrf2; bringing about its phosphorylation, subsequent nuclear translocation, and increases levels of its effector protein superoxide dismutase 2 (SOD2)[2]. Animal Model: Balb/c mice are born into and maintained in dim cyclic light[2] Dosage: 100 mg/kg; Administration: Intraperitoneal injection; for 6, 24 or 48 hours Result: Increased expression and activation of Nrf2 via phosphorylation on serine 40, increased expression of its target antioxidant superoxide dismutase 2 (SOD2), and reduced mitochondrial oxidative stress.
References

[1]. Wyse Jackson AC, et al. The synthetic progesterone Norgestrel is neuroprotective in stressed photoreceptor-like cellsand retinal explants, mediating its effects via basic fibroblast growth factor, protein kinase A and glycogen synthase kinase 3β signalling. Eur J Neurosci. 2016 Apr;43(7):899-911.

[2]. Byrne AM, et al. The synthetic progestin norgestrel modulates Nrf2 signaling and acts as an antioxidant in a model of retinal degeneration. Redox Biol. 2016 Dec;10:128-139.

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Boiling Point 459.1±45.0 °C at 760 mmHg
Melting Point 239-241ºC
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 :
JF8225200
CHEMICAL NAME :
18,19-Dinor-17-alpha-pregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-, (+-)-
CAS REGISTRY NUMBER :
6533-00-2
LAST UPDATED :
199109
DATA ITEMS CITED :
27
MOLECULAR FORMULA :
C21-H28-O2
MOLECULAR WEIGHT :
312.49
WISWESSER LINE NOTATION :
L E5 B666 OV MUTJ E2 FQ F1UU1 -DL

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
5010 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 18,185,1971
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
11200 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Liver - other changes
REFERENCE :
YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 29,1479,1978
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Liver - other changes
REFERENCE :
YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 29,1479,1978
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
5010 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 18,185,1971
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
7300 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Liver - other changes
REFERENCE :
YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 29,1479,1978
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>9 gm/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Liver - other changes
REFERENCE :
YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 29,1479,1978 ** TUMORIGENIC DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
57 mg/kg/68W-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 :
18 ug/kg
SEX/DURATION :
female 12 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - ovaries, fallopian tubes
REFERENCE :
FESTAS Fertility and Sterility. (American Fertility Soc., 608 13th Ave. S, Birmingham, AL 35282) V.1- 1950- Volume(issue)/page/year: 23,739,1972
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
4 mg/kg
SEX/DURATION :
female 40 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 :
INJFA3 International Journal of Fertility. (Allen Press, 1041 New Hampshire, St., Lawrence, KS 66044) V.1- 1955- Volume(issue)/page/year: 11,401,1966
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
365 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 :
BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 2,730,1969
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
75 ug/kg
SEX/DURATION :
female 5 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - menstrual cycle changes or disorders 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: 12,589,1975
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
30 ug/kg
SEX/DURATION :
female 30 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 :
BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 4,489,1968
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
150 mg/kg
SEX/DURATION :
female 15-24 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - parturition
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: 123,867,1966
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
525 mg/kg
SEX/DURATION :
female 35 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 :
INJFA3 International Journal of Fertility. (Allen Press, 1041 New Hampshire, St., Lawrence, KS 66044) V.1- 1955- Volume(issue)/page/year: 11,389,1966
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
548 ug/kg
SEX/DURATION :
female 49 week(s) pre-mating female 1-22 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 :
CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 2,59,1970
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
210 mg/kg
SEX/DURATION :
female 14 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - uterus, cervix, vagina
REFERENCE :
FESTAS Fertility and Sterility. (American Fertility Soc., 608 13th Ave. S, Birmingham, AL 35282) V.1- 1950- Volume(issue)/page/year: 24,284,1973
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
5 mg/kg
SEX/DURATION :
female 15-24 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - parturition
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: 123,867,1966
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
60 mg/kg
SEX/DURATION :
female 17-20 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - urogenital system
REFERENCE :
AVBIB9 Advances in the Biosciences. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1- 1967- Volume(issue)/page/year: 13,71,1974
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
700 ug/kg
SEX/DURATION :
female 14 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - ovaries, fallopian tubes 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: 5,57,1972
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
140 mg/kg
SEX/DURATION :
female 14 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: 5,57,1972
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
DOSE :
12 mg/kg
SEX/DURATION :
male 30 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands
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: 10,159,1972
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
DOSE :
19200 ug/kg
SEX/DURATION :
male 48 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)
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: 10,159,1972
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Implant
DOSE :
6 mg/kg
SEX/DURATION :
female 17 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
REFERENCE :
CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 12,549,1975
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
DOSE :
33 mg/kg
SEX/DURATION :
male 94 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - other effects on male
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: 7,49,1969
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
180 ug/kg
SEX/DURATION :
female 30 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - uterus, cervix, vagina Reproductive - Maternal Effects - other effects
REFERENCE :
IJMRAQ Indian Journal of Medical Research. (Indian Council of Medical Research, Ansari Nagar, New Delhi 110 029, India) V.1- 1913- Volume(issue)/page/year: 63,1413,1975
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Implant
DOSE :
600 ug/kg
SEX/DURATION :
female 17 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
REFERENCE :
CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 12,549,1975 *** REVIEWS *** TOXICOLOGY REVIEW JIMRBV Journal of International Medical Research. (Cambridge Medical Pub. Ltd., 435/437 Wellingborough Rd., Northampton, NN1 4EZ, UK) V.1- 1972- Volume(issue)/page/year: 1,141,1973

 Safety Information

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 JF8259000

 Articles29

More Articles
Progestagen-only oral contraceptives: a preliminary report of the action and clinical use of norgestrel and norethisterone.

Drugs 6(3) , 169-81, (1973)

Types of combined oral contraceptives used by US women.

Contraception 86(6) , 659-65, (2012)

We sought to estimate the prevalence of types of combined oral contraceptives (COCs) used among US women.We analyzed interview-collected data from 12,279 women aged 15-44 years participating in the Na...

Newer non-oral hormonal contraception.

BMJ 346 , f341, (2013)

 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
13-Ethyl-17-ethynyl-17b-hydroxy-4-gonen-3-one
17a-Ethynyl-18-homo-19-nortestosterone
Norgeston
13b-Ethyl-17a-ethynyl-17b-hydroxygon-4-en-3-one
18-METHYLNORETHINDRONE
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
monovar
MFCD01546387
sh850
wy3707
17b-Hydroxy-18-methyl-19-nor-17a-pregn-4-en-20-yn-3-one
(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
13-Ethyl-17-hydroxy-18,19-dinor-17a-pregn-4-en-20-yn-3-one
Norgestrel
17a-Ethynyl-13-ethyl-19-nortestosterone
Microlut
Ovrette
UNII:3J8Q1747Z2
D(−)-Norgestrel
NorLevo
(17a)-(-)-13-Ethyl-17-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one
D-(-)-Norgestrel
Neogest
(-)-Norgestrel
13-Ethyl-17a-ethynyl-17-hydroxygon-4-en-3-one
fh122-a
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