Norethisterone: Difference between revisions

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{{drugbox | IUPAC_name = (17β)-17-ethynyl-17-hydroxyestr-4-en-3-one |synonyms = <small>(8''R'',9''S'',10''R'',13''S'',14''S'',17''S'')-17-ethynyl-17-hydroxy-13-methyl-1,  2,6,7,8,9,10,11,12,14,15, 16-dodecahydrocyclopenta[''a'']phenanthren-3-one</small> | image = Norethisterone.png | CAS_number = 68-22-4 | ATC_prefix = G03 | ATC_suffix = AA05  | ATC_supplemental = | PubChem = 6230 | DrugBank = APRD00679 | C = 20 | H = 26 | O = 2 | molecular_weight = 298.419 g/mol | bioavailability =64%  | protein_bound = >95% | metabolism = | elimination_half-life = 7 hours | excretion = | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- Unscheduled / S2 / S4 / S8 --> | legal_UK = <!-- GSL / P / POM / CD --> | legal_US = <!-- OTC / Rx-only --> | legal_status = | routes_of_administration =
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==Overview==
'''Norethisterone''' (or '''norethindrone''') (or 19-nor-17α-ethynyltestosterone) is a molecule used in some [[combined oral contraceptive pill]]s and in some [[progestogen only pill]]s. 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. Norethindrone was the first orally highly active [[progestin]] to be synthesized.  It was synthesized for the first time by chemists Luis E. Miramontes, Carl Djerassi, and George Rosenkranz at Syntex in Mexico City in 1951.<ref>{{cite journal |author=Djerassi C, Miramontes L, Rosenkranz G, Sondheimer F |year=1954 |title=Steroids. LIV. Synthesis of 19-Nor-17α-ethynyltestosterone and 19-Nor-17α-methyltestosterone |journal=J Am Chem Soc |volume=76 |issue=16 |pages=4089&ndash;4091 |url=http://pubs.acs.org/cgi-bin/abstract.cgi/jacsat/1954/76/i16/f-pdf/f_ja01645a010.pdf |doi=10.1021/ja01645a009 |format=abstract page}}</ref> It was the progestin used in one of the first two [[combined oral contraceptive pill| oral contraceptive]]s.  It is often used as the related ester, [[norethisterone acetate]].


== References ==


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{{reflist|2}}
 
 
 
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{{Sex hormones}}








[[Category:Progestagens]]
[[de:Norethisteron]]


<!--Category-->
[[es:19-noretisterona]]


[[Category:Drug]]
[[pt:Noretindrona]]
{{WH}}
{{WS}}

Latest revision as of 16:26, 20 January 2015

Norethisterone
Clinical data
Synonyms(8R,9S,10R,13S,14S,17S)-17-ethynyl-17-hydroxy-13-methyl-1, 2,6,7,8,9,10,11,12,14,15, 16-dodecahydrocyclopenta[a]phenanthren-3-one
ATC code
Pharmacokinetic data
Bioavailability64%
Protein binding>95%
Elimination half-life7 hours
Identifiers
CAS Number
PubChem CID
DrugBank
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC20H26O2
Molar mass298.419 g/mol

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Overview

Norethisterone (or norethindrone) (or 19-nor-17α-ethynyltestosterone) is a molecule 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. Norethindrone was the first orally highly active progestin to be synthesized. It was synthesized for the first time by chemists Luis E. Miramontes, Carl Djerassi, and George Rosenkranz at Syntex in Mexico City in 1951.[1] It was the progestin used in one of the first two oral contraceptives. It is often used as the related ester, norethisterone acetate.

References

  1. ↑ Djerassi C, Miramontes L, Rosenkranz G, Sondheimer F (1954). "Steroids. LIV. Synthesis of 19-Nor-17α-ethynyltestosterone and 19-Nor-17α-methyltestosterone" (abstract page). J Am Chem Soc. 76 (16): 4089&ndash, 4091. doi:10.1021/ja01645a009.

Template:Sex hormones de:Norethisteron Template:WH Template:WS

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