Related Searches: 19-Norpregn-4-en-20-yn-3-one,17-hydroxy-, (17a)-, Estr-4-en-3-one,17-hydroxy-, (17b)-, Androst-4-en-3-one,17-(1-oxopropoxy)-, (17b)-, Estr-4-en-3-one,17-[(1-oxodecyl)oxy]-, (17b)-, Androst-4-en-3-one,17-[(1-oxodecyl)oxy]-, (17b)-, View all

19-Norpregn-4-en-20-yn-3-one,17-hydroxy-, (17a)-(CAS No. 68-22-4)

19-Norpregn-4-en-20-yn-3-one,17-hydroxy-, (17a)- C20H26O2 (cas 68-22-4) Molecular Structure

68-22-4 Structure

Identification and Related Records

【Name】
19-Norpregn-4-en-20-yn-3-one,17-hydroxy-, (17a)-
【Iupac name】
(8R,9S,10R,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,
11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
【CAS Registry number】
68-22-4
【Synonyms】
19-Norethisterone
17a-Ethynyl-19-nortestosterone
17-Hydroxy-19-nor-17a-pregn-4-en-20-yn-3-one
【EINECS(EC#)】
200-681-6
【Molecular Formula】
C20H26O2 (Products with the same molecular formula)
【Molecular Weight】
298.41924
【Inchi】
InChI=1S/C20H26O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,12,15-18,22H,4-11H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1
【InChIKey】
VIKNJXKGJWUCNN-XGXHKTLJSA-N
【Canonical SMILES】
CC12CCC3C(C1CCC2(C#C)O)CCC4=CC(=O)CCC34
【Isomers smiles】
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC(=O)CC[C@H]34
【MOL File】
68-22-4.mol

Chemical and Physical Properties

【Appearance】
Off-White to Pale Yellow Solid
【Density】
1.15 g/cm3
【Melting Point】
205-206℃
【Boiling Point】
447 °C at 760 mmHg
【Refractive Index】
1.577
【Flash Point】
447 °C at 760 mmHg
【Water】
chloroform: ≥50 mg/mL, clear, colorless
【Solubilities】
chloroform: ≥50 mg/mL, clear, colorless
【Color/Form】
white to off-white
【Storage temp】
-20°C Freezer
【Spectral properties】
Specific optical rotation: -31.7 @ 20 deg C/D (chloroform); first reported as -25 @ 20 deg C/D (chloroform); max absorption (ethanol): 240 nm (log e= 4.24)
【Computed Properties】
Molecular Weight:298.41924 [g/mol]
Molecular Formula:C20H26O2
XLogP3:3
H-Bond Donor:1
H-Bond Acceptor:2
Rotatable Bond Count:1
Tautomer Count:8
Exact Mass:298.19328
MonoIsotopic Mass:298.19328
Topological Polar Surface Area:37.3
Heavy Atom Count:22
Formal Charge:0
Complexity:594
Isotope Atom Count:0
Defined Atom Stereocenter Count:6
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Donor Count:1
Feature 3D Hydrophobe Count:1
Feature 3D Ring Count:4
Effective Rotor Count:1.8
Conformer Sampling RMSD:0.6
CID Conformer Count:2

Safety and Handling

【Hazard Codes】
Xn
【Risk Statements】
R40
【Safety Statements 】
22-36/37/39-45-26
【Safety】

Confirmed carcinogen with experimental carcinogenic, tumorigenic, and teratogenic data. Mildly toxic by ingestion. Human systemic effects by ingestion: dermatitis and androgenic effects. Human teratogenic effects: developmental abnormalities of the musculoskeletal system and urogenital system; and behavioral effects in the newborn. Human reproductive effects: spermatogenesis; testes, epididymis, sperm duct changes; impotence; male breast development; other male effects; ovaries, fallopian tube changes; menstrual cycle changes or disorders; uterus, cervix, vagina effects; postpartum effects; changes in female fertility. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

【Formulations/Preparations】
Norethisterone is available in the US as a grade containing 97-102% ai on an anhydrous basis.
NORETHINDRONE, USP (MICRONOR, NOR-QD, NORLUTIN), & NORETHINDRONE ACETATE, USP (NORLUTATE), ARE AVAIL ALONE IN 0.35-5-MG TABLETS & IN COMBINATION WITH ESTROGENS AS ORAL CONTRACEPTIVES.
【Exposure Standards and Regulations】
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
【Specification】

The 19-Norethisterone with the cas number 68-22-4, is also called (8R,9S,10R,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one. Its' system names are (1)19-Nor-17-alpha-pregn-4-en-20-yn-3-one, 17-hydroxy-; (2)19-Nor-17alpha-pregn-4-en-20-yn-3-one, 17-hydroxy- (8CI); (3)19-Norpregn-4-en-20-yn-3-one, 17-hydroxy-, (17alpha)-; (4)Norethisterone. And it belongs to the following product categories: (1)Active Pharmaceutical Ingredients; (2)Acetylenes; (3)Biochemistry; (4)Functionalized Acetylenes; (5)Hydroxyketosteroids; (6)Steroids; (7)Intermediates & Fine Chemicals; (8)Pharmaceuticals. It seems like off-white to pale yellow solid.

Physical properties about 19-Norethisterone are: (1)ACD/LogP: 3.38 ; (2)# of Rule of 5 Violations: 0 ; (3)ACD/LogD (pH 5.5): 3.38 ; (4)ACD/LogD (pH 7.4): 3.38 ; (5)ACD/BCF (pH 5.5): 219.89 ; (6)ACD/BCF (pH 7.4): 219.89 ; (7)ACD/KOC (pH 5.5): 1652.54 ; (8)ACD/KOC (pH 7.4): 1652.54 ; (9)#H bond acceptors: 2 ; (10)#H bond donors: 1 ; (11)#Freely Rotating Bonds: 1 ; (12)Polar Surface Area: 26.3??2 ; (13)Index of Refraction: 1.577 ; (14)Molar Refractivity: 85.55 cm3 ; (15)Molar Volume: 258 cm3 ; (16)Polarizability: 33.91 ×10-24cm3 ; (17)Surface Tension: 49 dyne/cm ; (18)Density: 1.15 g/cm3 ; (19)Flash Point: 190.5 °C ; (20)Enthalpy of Vaporization: 81.38 kJ/mol ; (21)Boiling Point: 447 °C at 760 mmHg ; (22)Vapour Pressure: 7.22E-10 mmHg at 25°C

Uses of 19-Norethisterone: It is used in some combined oral contraceptive pills and in some progestogen only pills. It is a progestogen and can be used to treat premenstrual syndrome, painful periods, abnormal heavy bleeding, irregular periods, menopausal syndrome (in combination with oestrogen), or to postpone a period.

When you are using this chemical, please be cautious about it as the following: It is not only irritating to eyes, respiratory system and skin but also harmful by inhalation, in contact with skin and if swallowed. And it shows limited evidence of a carcinogenic effect. Before you are using it, you would better wear suitable protective clothing, gloves and eye/face protection to avoid breathing dust. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.).

You can still convert the following datas into molecular structure :
(1).SMILES: O=C4\C=C3/[C@@H]([C@H]2CC[C@]1([C@@H](CC[C@]1(C#C)O)[C@@H]2CC3)C)CC4
(2).InChI:InChI=1/C20H26O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,12,15-18,22H,4-11H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s

Toxic information of 19-Norethisterone can be showed as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 6gm/kg (6000mg/kg) ? Drugs in Japan Vol. -, Pg. 809, 1990.
women TDLo oral 42mg/kg (42mg/kg) ENDOCRINE: ANDROGENIC

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
American Journal of Obstetrics and Gynecology. Vol. 84, Pg. 962, 1962.

【Octanol/Water Partition Coefficient】
log P = 2.97
【Report】
NTP 10th Report on Carcinogens. IARC Cancer Review: Animal Sufficient Evidence IMEMDT ?? IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 294.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.:?) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . EPA Genetic Toxicology Program.
Safety Profile

Confirmed carcinogen with experimental carcinogenic, tumorigenic, and teratogenic data. Mildly toxic by ingestion. Human systemic effects by ingestion: dermatitis and androgenic effects. Human teratogenic effects: developmental abnormalities of the musculoskeletal system and urogenital system; and behavioral effects in the newborn. Human reproductive effects: spermatogenesis; testes, epididymis, sperm duct changes; impotence; male breast development; other male effects; ovaries, fallopian tube changes; menstrual cycle changes or disorders; uterus, cervix, vagina effects; postpartum effects; changes in female fertility. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

The methyl ether of estrone is reacted with lithium metal in liquid ammonia to reduce Ring A to the 4-ene state and the reduced compound is then oxidized with chromic acid in aqueous acetic acid to form estr-4-ene-3,17-dione. In order to prevent the 3-keto group from participating in the ensuing ethynylation reaction, it is now with ethyl orthoformate in the presence of pyridine hydrochloride to form the 3-ethoxy-3,5-diene compound (II). Acetylene is then passed into a solution of compound II in toluene, previously admixed with a solution of sodium in t-amyl alcohol, to form the 17-ethynyl-17-hydroxy compound. Hydrolysis at the 3-ethyoxy linkage by heating with dilute HCl is accompanied by a rearrangement of the 3-hydroxy-3,5-diene compound to the 3-oxo-4- ene state.
From 19-nor-4-androstene-3,17-dione. U.S. pat. 2,744,122 (1956 to Syntex); DeRuggieri, U.S. pat. 2,849,462 (1958).
U.S. Exports

Total US sales for human medicine containing norethisterone have been estimated to have been <4,400 lb/yr prior to 1972 ... .
Consumption Patterns

Since 1962, the most common use in the US has been as the progestin in progestin-estrogen combination oral contraceptives.
【Usage】

Progesteron. Norethindrone and acetate in combination with estrogen as contraceptive (oral). It is reasonably anticipated to be a human carcinogen

Biomedical Effects and Toxicity

【Pharmacological Action】
- Oral contraceptives which owe their effectiveness to synthetic preparations.
【Therapeutic Uses】
Contraceptives, Oral, Synthetic; Progestational Hormones, Synthetic
RESULTS OF RECENT STUDIES HAVE SHOWN THAT THIS PROGESTATIONAL AGENT, WHEN USED IN CONJUNCTION WITH APPROPRIATE DIET, DECR VLDL & CHYLOMICRONS IN SOME WOMEN WITH TYPE V HYPERLIPOPROTEINEMIA... THERE IS CONCURRENT INCR IN PHLA /POST-HEPARIN LIPOLYTIC ACTIVITY/ & AMELIORATION OF ABDOMINAL PAIN OR PANCREATITIS.
FOR AMENORRHEA, DYSFUNCTIONAL UTERINE BLEEDING, PREMENSTRUAL TENSION, OR DYSMENORRHEA ...; FOR ENDOMETRIOSIS ...; FOR CONTRACEPTION...
...IT IS 2-3 TIMES AS POTENT AS PARENT STEROID. /ACETATE/
VET: ITS USE IN POULTRY DELAYS SEXUAL MATURITY OF PULLETS & POULTS, & STOPS EGG PRODN IN HENS. IT POSSESSES BOTH ANDROGENIC & ANABOLIC EFFECTS... THIS HAS PROMPTED TRIALS WITH SWINE TO DELAY ONSET OF PUBERTY & ESTRUS FOR 3-5 MO IN GILTS & TO INCR THEIR DAILY WT GAINS. TREATED BOARS IGNORE SOWS IN HEAT...
To delay or prevent menstruation, it is given in doses of 15-30 mg daily ... .
Norethindrone acetate ... /is/ indicated in the treatment of menstrual disorders, including secondary amenorrhea and dysfunctional uterine bleeding (DUB) caused by hormonal imbalance in the absence of organic pathology. ... The uterus must be sufficiently primed with endogenous or exogenous estrogen for the progestins to produce a secretory-like endometrium and endometrial shedding after progestin use ends. Withdrawal bleeding usually occurs 3 to 7 days after discontinuation of the progestin for women with an intact uterus. /Included in US product labeling/
Norethindrone acetate ... /is/ indicated in the treatment of endometriosis. /Included in US product labeling/
Norethindrone ... can be used to oppose the effects of estrogen on the endometrium in menopausal women who take estrogens for ovarian hormone therapy (OHT), also called hormone replacement therapy (HRT) and estrogen replacement therapy (ERT). All menopausal patients receiving progestins do not have recognized endometrial shedding; there is frequently amenorrhea after several months of treatment with estrogen-progestin regimens. The optimal or recommended length for estrogen replacement after menopause has not been established. Studies have shown that administration of a progestin for a minimum of 10 to 14 days of an estrogen cycle in women with an intact uterus is required for major reduction of endometrial hyperplasia and endometrail carcinoma compared with an estrogen-only cycle. Other dosing regimens for estrogens and progestins, including low continuous daily dosing, are also used. Progestins without estrogens may be used for debilitating menopausal symptoms in patients who have had breast cancer and are candidates for progestin therapy but cannot take estrogens. /NOT included in US product labeling/
For prevention, norethindrone can be used to oppose the effects of estrogen on the endometrium in menopausal women who take estrogens for ovarian hormone therapy (OHT), also called hormone replacement therapy (HRT) and estrogen replacement therapy (ERT). All menopausal patients receiving progestins do not have recognized endometrial shedding; there is frequently amenorrhea after several months of treatment with estrogen-progestin regimens. The optimal or recommended length for estrogen replacement after menopause has not been established. Studies have shown that administration of a progestin for a minimum of 10 to 14 days of an estrogen cycle in women with an intact uterus is required for major reduction of endometrial hyperplasia and endometrial carcinoma compared with an estrogen-only cycle. Other dosing regimens for estrogens and progestins without estrogens and progestins, including low continuous daily dosing, are also used. Progestins without estrogens may be used for debilitating menopausal symptoms in patients who have breast cancer and are candidates for progestin therapy but cannot take estrogens. /NOT included in US product labeling/
【Biomedical Effects and Toxicity】
...NORETHINDRONE.../APPEARS/ TO BIND TO INTESTINAL WALL & ARE THEN SLOWLY RELEASED INTO BLOODSTREAM.
IN WOMEN GIVEN 15,16,3H-NORETHINDRONE ACETATE 20 MUCI IV IN 10% ETHANOL-WATER VEHICLE, NORETHINDRONE HAD BIPHASIC DISAPPEARANCE WITH RAPID INITIAL DISAPPEARANCE IN 1ST 6 HR FOLLOWED BY SLOW DISAPPEARANCE PHASE (34.8 HR). RESULTS ARE COMPARED WITH OTHER PROGESTINS DATA.
In 25 BALB/c mice implanted subcutaneously with pellets containing 40% norethisterone and 60% cholesterol for 76-77 wk, absorption of norethisterone was estimated to be between 3.6 and 15.9 ug/day (mean, 7.7 ug/day).
Rabbits excrete norethisterone metabolites predominantly in the urine ... while rats excrete them to 80% in bile ... .
When 3H- or 14C-norethisterone was given orally to men, about half of the dose was excreted in the urine ...
Although norethisterone is absorbed almost completely, it undergoes first-pass metabolism, which decreases its bioavailability to an average of 64%. There is wide inter individual variation in its absorption, which is estimated to be has high as three- to fivefold. Norethisterone is absorbed rapidly, achieving maximum serum concentrations within 1-4 hours. After doses of 0.5, 1 and 3 mg, the serum concentrations peaked at 2-5, 5-10 and up to 30 ng/ml, respectively.

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