CAS 68-22-4|17-羟基-19-去甲-17α-孕甾-4-烯-20-炔基-3-酮|(1S,2R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-15-methyltetracyclo[8.7.0.02,7.011,1...

基本信息

化学结构

分子式

C₂₀H₂₆O₂

分子量

298.41924

精确质量

298.19328007

电荷

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

Canonic Smiles

C#C[C@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@H]12

Isomeric Smiles

O[C@@]1([C@@]2([C@H]([C@H]3[C@H](CC2)[C@@H]2C(=CC(=O)CC2)CC3)CC1)C)C#C

计算属性

JChem

LogD (pH = 7.4)

3.22

LogD (pH = 5.5)

3.22

Log P

3.22

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

true

Acid pKa

-1.66

极化表面积

37.30

极化性

34.71

摩尔折射率

87.42

LOG S

-4.78

数据来源

名称和标识

别名

17-羟基-19-去甲-17α-孕甾-4-烯-20-炔基-3-酮17α-乙炔基-17β-羟基-19-去甲-4-雄甾烯-3-酮炔诺酮19-Norethindrone去甲基脱氢羟孕酮17α-乙炔基-19-去甲睾酮19-去甲-17α-乙炔基-4-雄甾烯-17β-醇-3-酮Norethindrone17α-Ethynyl-19-nortestosterone17α-Ethynyl-17 β-hydroxy-19-nor-4-androsten-3-one(8R,9S,10R,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one19-Norethisterone19-Nor-17α-ethynyl-4-androsten-17β-ol-3-one17α-Ethynyl-19-nortestosterone17α-Ethynyl-17β-hydroxy-19-nor-4-androsten-3-one17-Hydroxy-19-nor-17α-4-pregnen-20-yn-3-one19-nor-17alpha-ethynylandrosten-17beta-ol-3-one17alpha-ethynyl-4-estren-17-ol-3-oneMicronor19-nor-17alpha-ethynyl-17beta-hydroxy-4-androsten-3-one(17alpha)-17-ethynyl-17-hydroxyestra-4,8(14),9-trien-3-one17alpha-ethynyl-17-hydroxy-4-estren-3-one17-beta-hydroxy-19-norpregn-4-en-20-yn-3-one17alpha-ethynyl-17beta-hydroxy-19-norandrost-4-en-3-one17-alpha-ethynyl-17-hydroxy-4-estren-3-one17beta-hydroxy-19-norpregn-4-en-20-yn-3-one19-nor-17-alpha-ethynylandrosten-17-beta-ol-3-one19-Norethisterone17alpha-ethinylestra-4-en-17beta-ol-3-onenorethisterone17-hydroxy-19-nor-17-alpha-pregn-4-en-20-yn-3-one17alpha-ethynyl-19-norandrost-4-en-17beta-ol-3-one17alpha-ethinyl-19-nortestosterone19-nor-17alpha-ethynyltestosteroneNorethisteron17alpha-ethynyl-19-nortestosterone17alpha-ethynyl-19-nor-4-androsten-17beta-ol-3-one4-estren-17alpha-ethynyl-17beta-ol-3-one17-alpha-ethynyl-4-estren-17-ol-3-onePrimolut-N19-nor-ethindrone17-alpha-ethynyl-19-norandrost-4-en-17-beta-ol-3-one17-alpha-ethynyl-19-nortestosteronenorethindrone17-hydroxy-19-nor-17alpha-pregn-4-en-20-yn-3-one19-norethisterone19-Nor-17alpha-ethynyl-17beta-hydroxy-4-androsten-3-one19-nor-17-alpha-ethynyltestosterone19-nor-17-alpha-ethynyl-17-beta-hydroxy-4-androsten-3-one

IUPAC标准名

(1S,2R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one (1S,2R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one (1R,3aS,3bR,9aR,9bS,11aS)-1-ethynyl-1-hydroxy-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one

IUPAC传统名

norethindrone

商标名

TriellaOvysmen 1 35NoraethisteronumNoralutinNorinylNor-QdTrinovumNorethisteronum [INN-Latin]NorforJenest-28LoestrinNorcolutEstrinorMenzolBrevinor 21UtovlanNorethisterone [Progestins]MinovlarNETNeconEthynylmortestosteroneNorethin 1/35 ENoretisterona [INN-Spanish]Norethindrone AcetateNorethinPalonylNorethadroneNor-Q.D.NormapauseMilliNorpregneninloneNorethynodroneMicronettTri-NorinylLoestrin 24 FeBrevinor-1 28OvysmenPrimolut NMini-PeBreviconNelovaConludafPrimolut-NCamilaNoriday 28Mini-PillModiconBrevinor-1 21OrlestJenestOrtho 1 35SynphaseMicronethN.E.E.BinovumProluteasiNodiolNorethisteronOrtho-Novum 1 50Norethin 1/50 MNorethyndronAnovulatorioDemulenTrinovum 21ConludagNoretisterone [Dcit]Synphasic 28Ortho-NovumMicronovumNorlestrinNorlutenNoresthisteroneAygestinENTAnovuleBrevinor 28BrevinorUtovlarNorpregneninotoneOrtho-Novum 7 7 7Ovysmen 0.5 35NoriminNorlutateNorpregneninoloneOrtho-Novum 1 35Norethindrone NorethisteroneNorcept-ENorlutonNorethynodronAnhydrohydroxynorprogesteroneNorlutinNeoconEthinylnortestosteroneOrtho 7 7 7NorceptCiclovulanConceplanEthynylnortestosteronePerovexGenoraOvconGestestErrinNorethisteroneNorgestinNoridayMicronorGenceptMini-peMini-pill

国际非专利药品(INN)

norethisteronumnorethisteronenoretisterona

名称和标识

数据登录号

Beilstein号

1915671

PubChem SID

16096406124897669248702594650481650139262

CAS号

PubChem CID

MDL号

EC号

LIPID MAPS Instance

专利号

US2007196453US2007196452EP1666044EP1535618US2007185068US2007189977US2007264345EP1862167US2007196323US2007197488US2007248658EP1547600

DrugBank ID

DB00717

Drug Central Database

1,962

MetaboLights数据库

MTBLS1918MTBLS2406MTBLS2291MTBLS3038MTBLS1622MTBLS3750MTBLS2145MTBLS1693

CHEMBL

CHEMBL1162

SABIO-RK数据库

7911

CHEBI ID

CHEBI:44349CHEBI:7627

PubMed文献链接

1208382186052324019188

Reaxys Registry

PDBeChem数据库

CompTox数据库

PDB数据库

KEGG ID

ACToR数据库

BindingDB数据库

HMDB数据库

SureChEMBL数据库

KEGG DRUG Database

维基百科标题

数据登录号

化合物性质

理化性质

疏水性(logP)

3.2

溶解度

7.04 mg/L

chloroform: ≥50 mg/mL, clear, colorless

熔点

203-204 °C

205-206 °C(lit.)

外观

white to off-white powder

[α]20/D -24°, c = 1 in chloroform

安全信息

下载链接

R:45

药理学性质

human ... AR(367), PGR(5241)rat ... Ar(24208)

化合物性质

分子相关蛋白质

分子图谱

暂无数据

点击上传数据

描述信息

DrugBank

DB00717

Drug Groups

approved

Description

A synthetic progestational hormone with actions similar to those of progesterone but functioning as a more potent inhibitor of ovulation. It has weak estrogenic and androgenic properties. The hormone has been used in treating amenorrhea, functional uterine bleeding, endometriosis, and for contraception. [PubChem]

Indication

For use as an oral contraceptive in the prevention of pregnancy.

Pharmacology

Norethindrone is a synthetic oral progestin. It is used for contraception or to treat such conditions as secondary amenorrhea, abnormal uterine bleeding, and endometriosis. As an oral contraceptive, norethindrone is available as either a single agent or in combination with an estrogen.

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic

Absorption

Absolute oral bioavailability approximately 64%

Half Life

7 hours

Protein Binding

>95%

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

MP Biomedicals

02155946

(17α-Ethynyl-17β-hydroxy-19-nor-4-androsten-3-one; 17α-Ethynyl-19-nortestosterone) Crystalline

Sigma Aldrich

N6384

Biochem/physiol Actions
炔诺酮是用于抑制细胞溶质磺基转移酶类 (SULT) 的口服避孕药。
包装
Supplied in amber screw-cap vials

N4128

Biochem/physiol Actions
炔诺酮是用于抑制细胞溶质磺基转移酶类 (SULT) 的口服避孕药。
包装
1, 5 g in glass bottle
250 mg in glass bottle
50 mg in poly bottle

286850

Biochem/physiol Actions
炔诺酮是用于抑制细胞溶质磺基转移酶类 (SULT) 的口服避孕药。

46525

Biochem/physiol Actions
炔诺酮是用于抑制细胞溶质磺基转移酶类 (SULT) 的口服避孕药。
法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

ChEBI

CHEBI:7627

A 17beta-hydroxy steroid that is testosterone in which the hydrogen at position 17 is replaced by an ethynyl group and in which the methyl group attached to position 10 is replaced by hydrogen.

描述信息

参考文献

PubChem文献

暂无数据

点击上传数据

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

别名

IUPAC标准名

IUPAC传统名

norethindrone

商标名

国际非专利药品(INN)

norethisteronumnorethisteronenoretisterona

数据登录号

Beilstein号

1915671

PubChem SID

16096406124897669248702594650481650139262

CAS号

PubChem CID

MDL号

EC号

LIPID MAPS Instance

专利号

US2007196453US2007196452EP1666044EP1535618US2007185068US2007189977US2007264345EP1862167US2007196323US2007197488US2007248658EP1547600

DrugBank ID

DB00717

Drug Central Database

1,962

MetaboLights数据库

MTBLS1918MTBLS2406MTBLS2291MTBLS3038MTBLS1622MTBLS3750MTBLS2145MTBLS1693

CHEMBL

CHEMBL1162

SABIO-RK数据库

7911

CHEBI ID

CHEBI:44349CHEBI:7627

PubMed文献链接

1208382186052324019188

Reaxys Registry

PDBeChem数据库

CompTox数据库

PDB数据库

KEGG ID

ACToR数据库

BindingDB数据库

HMDB数据库

SureChEMBL数据库

KEGG DRUG Database

维基百科标题

描述信息

DB00717

Drug Groups

approved

Description

Indication

For use as an oral contraceptive in the prevention of pregnancy.

Pharmacology

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic

Absorption

Absolute oral bioavailability approximately 64%

Half Life

7 hours

Protein Binding

>95%

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

MP Biomedicals

02155946

(17α-Ethynyl-17β-hydroxy-19-nor-4-androsten-3-one; 17α-Ethynyl-19-nortestosterone) Crystalline

Sigma Aldrich

N6384

Biochem/physiol Actions
炔诺酮是用于抑制细胞溶质磺基转移酶类 (SULT) 的口服避孕药。
包装
Supplied in amber screw-cap vials

N4128

Biochem/physiol Actions
炔诺酮是用于抑制细胞溶质磺基转移酶类 (SULT) 的口服避孕药。
包装
1, 5 g in glass bottle
250 mg in glass bottle
50 mg in poly bottle

286850

Biochem/physiol Actions
炔诺酮是用于抑制细胞溶质磺基转移酶类 (SULT) 的口服避孕药。

46525

Biochem/physiol Actions
炔诺酮是用于抑制细胞溶质磺基转移酶类 (SULT) 的口服避孕药。
法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

ChEBI

CHEBI:7627

A 17beta-hydroxy steroid that is testosterone in which the hydrogen at position 17 is replaced by an ethynyl group and in which the methyl group attached to position 10 is replaced by hydrogen.

参考文献

PubChem文献

暂无数据

点击上传数据

生物活性

PubChem BioAssay

化合物性质

理化性质

疏水性(logP)

3.2

溶解度

7.04 mg/L

chloroform: ≥50 mg/mL, clear, colorless

熔点

203-204 °C

205-206 °C(lit.)

外观

white to off-white powder

[α]20/D -24°, c = 1 in chloroform

安全信息

下载链接

R:45

药理学性质

human ... AR(367), PGR(5241)rat ... Ar(24208)

化合物信息

ID:598