CAS 17230-88-5|Chronogyn|Danazol|(1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.0^{2,10}.0^{4,8}.0^{14,18}]icosa-4(8),5,9-trien-17-ol|Cyclomen|Danocrine|Anatrol|danazo...

General Information

Structure

Molecular Formula

C₂₂H₂₇NO₂

Molecular Mass

337.45528

Exact Mass

337.20417911

Charge

InChI

InChI=1S/C22H27NO2/c1-4-22(24)10-8-18-16-6-5-15-11-19-14(13-23-25-19)12-20(15,2)17(16)7-9-21(18,22)3/h1,11,13,16-18,24H,5-10,12H2,2-3H3/t16-,17+,18+,20+,21+,22+/m1/s1

InChIKey

POZRVZJJTULAOH-LHZXLZLDSA-N

Canonic Smiles

C#C[C@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=Cc3c(C[C@]12C)cno3

Isomeric Smiles

O[C@@]1([C@@]2([C@H]([C@H]3[C@@H]([C@@]4(C(=Cc5oncc5C4)CC3)C)CC2)CC1)C)C#C

Calculated Properties

JChem

Acid pKa

17.594933

H Acceptors

H Donor

LogD (pH = 5.5)

3.4620798

LogD (pH = 7.4)

3.4620821

Log P

3.4620821

Molar Refractivity

98.5352

Polarizability

37.660843

Polar Surface Area

46.26

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

3.62

LOG S

-4.28

Solubility (Water)

1.76e-02 g/l

Data Source

Names and Identifiers

Brand Name

ChronogynCyclomenDanocrineAnatrol

Synonyms

Danazol2,4,17α-Pregnadien-20-yno[2,3-d]-isoxa-zol-17-ol17β-Hydroxy-2,4,17α-pregnadien-20-yno[2,3-d]-isoxazole17β-hydroxy-2,4,17α-pregnadien-20-yno[2,3-D]isoxazoleDanol(17α)-Pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-olWin-17757CyclomenBonzolDanatrolDanocrine17α-Ethynyl-17β-hydroxy-4-androsteno[2,3-d]isoxazole

IUPAC name

(1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.0^{2,10}.0^{4,8}.0^{14,18}]icosa-4(8),5,9-trien-17-ol (1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icosa-4(8),5,9-trien-17-ol

IUPAC Traditional name

danazol

Names and Identifiers

Registration numbers

EC Number

CAS Number

PubChem CID

PubChem SID

ATC CODE

KEGG ID

Wikipedia Title

CHEMBL

CHEBI ID

Unique Ingredient Identifier

Medline Plus

DrugBank ID

Chemspider ID

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

0.51 [PERRISSOUD,D & TESTA,B (1986)]

Melting Point

225°C (dec.)

218-2200C

Solubility

Acetonitrile

Ethanol

Chloroform

Apperance

Off-White to Pale Yellow Solid

Product Information

Certificate of Analysis

Download link

Classification

Rare Derivatives of Natural Compounds

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB01406

Drug Groups

approved

Description

A synthetic steroid with antigonadotropic and anti-estrogenic activities that acts as an anterior pituitary suppressant by inhibiting the pituitary output of gonadotropins. It possesses some androgenic properties. Danazol has been used in the treatment of endometriosis and some benign breast disorders. [PubChem]

Indication

For the treatment of endometriosis and fibrocystic breast disease (in patients unresponsive to simple measures). Also used for the prophylactic treatment of all types of hereditary angioedema in males and females.

Pharmacology

Danazol is a derivative of the synthetic steroid ethisterone, a modified testosterone. It was approved by the U.S. Food and Drug Administration (FDA) as the first drug to specifically treat endometriosis, but its role as a treatment for endometriosis has been largely replaced by the gonadotropin-releasing hormone (GnRH) agonists. Danazol has antigonadotropic and anti-estrogenic activities. Danazol acts as an anterior pituitary suppressant by inhibiting the pituitary output of gonadotropins. It possesses some androgenic properties.

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic, to principal metabolites, ethisterone and 17-hydroxymethylethisterone.

Half Life

Approximately 24 hours.

References

• Dmowski WP: Danazol. A synthetic steroid with diverse biologic effects. J Reprod Med. 1990 Jan;35(1 Suppl):69-74; discussion 74-5. [Pubmed]

• Donaldson VH: Danazol. Am J Med. 1989 Sep;87(3N):49N-55N. [Pubmed]

• Jenkin G: Review: The mechanism of action of danazol, a novel steroid derivative. Aust N Z J Obstet Gynaecol. 1980 May;20(2):113-8. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Wikipedia

Danazol

TRC

D145000

Danazol is an anterior pituitary supressant. Danazol is an anabolic steroid derivative of ethisterone, with mild androgenic side effects (an impeded androgen). Antigonadotropin.

Molecule Details

References

PubChem Literature

From Data Sources

• Jenkin G: Review: The mechanism of action of danazol, a novel steroid derivative. Aust N Z J Obstet Gynaecol. 1980 May;20(2):113-8. Pubmed

• Donaldson VH: Danazol. Am J Med. 1989 Sep;87(3N):49N-55N. Pubmed

• Dmowski WP: Danazol. A synthetic steroid with diverse biologic effects. J Reprod Med. 1990 Jan;35(1 Suppl):69-74; discussion 74-5. Pubmed

• Ahn, Y.S., et al.: N. Engl. J. Med., 308, 1396 (1983)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Brand Name

ChronogynCyclomenDanocrineAnatrol

Synonyms

IUPAC name

IUPAC Traditional name

danazol

Registration numbers

EC Number

CAS Number

PubChem CID

PubChem SID

ATC CODE

KEGG ID

Wikipedia Title

CHEMBL

CHEBI ID

Unique Ingredient Identifier

Medline Plus

DrugBank ID

Chemspider ID

Molecule Details

DB01406

Drug Groups

approved

Description

Indication

Pharmacology

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic, to principal metabolites, ethisterone and 17-hydroxymethylethisterone.

Half Life

Approximately 24 hours.

References

• Dmowski WP: Danazol. A synthetic steroid with diverse biologic effects. J Reprod Med. 1990 Jan;35(1 Suppl):69-74; discussion 74-5. [Pubmed]

• Donaldson VH: Danazol. Am J Med. 1989 Sep;87(3N):49N-55N. [Pubmed]

• Jenkin G: Review: The mechanism of action of danazol, a novel steroid derivative. Aust N Z J Obstet Gynaecol. 1980 May;20(2):113-8. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Wikipedia

Danazol

TRC

D145000

Danazol is an anterior pituitary supressant. Danazol is an anabolic steroid derivative of ethisterone, with mild androgenic side effects (an impeded androgen). Antigonadotropin.

References

PubChem Literature

From Data Sources

• Jenkin G: Review: The mechanism of action of danazol, a novel steroid derivative. Aust N Z J Obstet Gynaecol. 1980 May;20(2):113-8. Pubmed

• Donaldson VH: Danazol. Am J Med. 1989 Sep;87(3N):49N-55N. Pubmed

• Dmowski WP: Danazol. A synthetic steroid with diverse biologic effects. J Reprod Med. 1990 Jan;35(1 Suppl):69-74; discussion 74-5. Pubmed

• Ahn, Y.S., et al.: N. Engl. J. Med., 308, 1396 (1983)

Bioactivity

PubChem BioAssay

Properties

Physical Property

Hydrophobicity(logP)

0.51 [PERRISSOUD,D & TESTA,B (1986)]

Melting Point

225°C (dec.)

218-2200C

Solubility

Acetonitrile

Ethanol

Chloroform

Apperance

Off-White to Pale Yellow Solid

Product Information

Certificate of Analysis

Download link

Classification

Rare Derivatives of Natural Compounds

Molecule

ID:1215