Danazol

Identification

Summary

Danazol is a synthetic steroid and pituitary gonadotropin inhibitor used in the treatment of endometriosis and symptomatic treatment of severe pain and tenderness associated with benign fibrocystic breasts.

Brand Names
Cyclomen
Generic Name
Danazol
DrugBank Accession Number
DB01406
Background

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.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 337.4553
Monoisotopic: 337.204179113
Chemical Formula
C22H27NO2
Synonyms
  • Danazol
  • Danazolum
External IDs
  • WIN 17,757
  • WIN-17757

Pharmacology

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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofEndometriosis••••••••••••
Symptomatic treatment ofFibrocystic breast disease••••••••••••
Management ofHereditary angioedema••••••••••••
Management ofRefractory immune thrombocytopenia••• •••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

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.

Mechanism of action

As a gonadotropin inhibitor, danazol suppresses the pituitary-ovarian axis possibly by inhibiting the output of pituitary gonadotropins. Danazol also depresses the preovulatory surge in output of follicle-stimulating hormone (FSH) and luteinizing hormone (LH), thereby reducing ovarian estrogen production. Danazol may also directly inhibits ovarian steroidogenesis; bind to androgen, progesterone, and glucocorticoid receptors; bind to sex-hormone-binding globulin and corticosteroid-binding globulin; and increases the metabolic clearance rate of progesterone. Another mechanism of action by which danazol may use to facilitate regression of endometriosis is by decreasing IgG, IgM, and IgA concentrations, as well as phospholipid and IgG isotope autoantibodies. In the treatment of endometriosis, as a consequence of suppression of ovarian function, danazol causes both normal and ectopic endometrial tissues to become inactive and atrophic. This leads to anovulation and associated amenorrhea. In fibrocystic breast disease, the exact mechanism of action of danazol is unknown, but may be related to suppressed estrogenic stimulation as a result of decreased ovarian production of estrogen. A direct effect on steroid receptor sites in breast tissue is also possible. This leads to a disappearance of nodularity, relief of pain and tenderness, and possibly changes in the menstrual pattern. In terms of hereditary angioedema, danazol corrects the underlying biochemical deficiency by increasing serum concentrations of the deficient C1 esterase inhibitor, resulting in increased serum concentrations of the C4 component of the complement system. (Source: PharmGKB)

TargetActionsOrganism
AEstrogen receptor alpha
agonist
Humans
AAndrogen receptor
agonist
Humans
AProgesterone receptor
agonist
Humans
AGonadotropin-releasing hormone receptor
negative modulator
Humans
APutative gonadotropin-releasing hormone II receptor
negative modulator
Humans
UC-C motif chemokine 2
inhibitor
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

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

Hover over products below to view reaction partners

Route of elimination

Not Available

Half-life

Approximately 24 hours.

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe metabolism of 1,2-Benzodiazepine can be decreased when combined with Danazol.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Danazol.
AbirateroneThe metabolism of Abiraterone can be decreased when combined with Danazol.
AcalabrutinibThe metabolism of Acalabrutinib can be decreased when combined with Danazol.
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Danazol.
Food Interactions
  • Take with or without food. The absorption is unaffected by food.

Products

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Product Images
International/Other Brands
Danol (Sanofi)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CyclomenCapsule200 mgOralSanofi Aventis1972-12-31Not applicableCanada flag
CyclomenCapsule100 mgOralSanofi Aventis1976-12-31Not applicableCanada flag
CyclomenCapsule50 mgOralSanofi Aventis1980-12-31Not applicableCanada flag
DanocrineCapsule100 mg/1OralSanofi Aventis1976-06-212004-12-14US flag
DanocrineCapsule50 mg/1OralSanofi Aventis1976-06-212004-12-14US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
DanazolCapsule200 mg/1OralAmerincan Health Packaging2008-08-272014-09-30US flag
DanazolCapsule200 mg/1OralProficient Rx LP2005-09-28Not applicableUS flag
DanazolCapsule100 mg/1OralLannett Company, Inc.2007-04-19Not applicableUS flag
DanazolCapsule100 mg/1OralTeva Pharmaceuticals USA, Inc.1998-06-25Not applicableUS flag
DanazolCapsule100 mg/1OralChartwell Rx, Llc.2007-04-19Not applicableUS flag

Categories

ATC Codes
G03XA01 — Danazol
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Estrane steroids
Direct Parent
Estrane steroids
Alternative Parents
17-hydroxysteroids / Ynones / Tertiary alcohols / Isoxazoles / Heteroaromatic compounds / Cyclic alcohols and derivatives / Oxacyclic compounds / Azacyclic compounds / Acetylides / Organopnictogen compounds
show 2 more
Substituents
17-hydroxysteroid / Acetylide / Alcohol / Aromatic heteropolycyclic compound / Azacycle / Azole / Cyclic alcohol / Estrane-skeleton / Heteroaromatic compound / Hydrocarbon derivative
show 11 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
terminal acetylenic compound, 17beta-hydroxy steroid (CHEBI:4315)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
N29QWW3BUO
CAS number
17230-88-5
InChI Key
POZRVZJJTULAOH-LHZXLZLDSA-N
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
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
SMILES
[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC3=C(C[C@]12C)C=NO3

References

Synthesis Reference

Clinton, R. and Hanson, A.; US. Patent 3,135,743; June 2, 1964; assigned to Sterling Drug.

General References
  1. Dmowski WP: Danazol. A synthetic steroid with diverse biologic effects. J Reprod Med. 1990 Jan;35(1 Suppl):69-74; discussion 74-5. [Article]
  2. Donaldson VH: Danazol. Am J Med. 1989 Sep;87(3N):49N-55N. [Article]
  3. 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. [Article]
Human Metabolome Database
HMDB0002835
KEGG Drug
D00289
PubChem Compound
28417
PubChem Substance
46506475
ChemSpider
26436
BindingDB
50423541
RxNav
3102
ChEBI
4315
ChEMBL
CHEMBL1479
ZINC
ZINC000003881958
Therapeutic Targets Database
DAP001017
PharmGKB
PA164749056
PDBe Ligand
QA1
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Danazol
PDB Entries
6ulb
MSDS
Download (75 KB)

Clinical Trials

Clinical Trials

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Amerisource Health Services Corp.
  • Barr Pharmaceuticals
  • Kaiser Foundation Hospital
  • Lannett Co. Inc.
  • Medisca Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Physicians Total Care Inc.
  • Sanofi-Aventis Inc.
Dosage Forms
FormRouteStrength
CapsuleOral
CapsuleOral50 mg
Powder1 kg/1kg
Capsule, coatedOral100 mg
Capsule, coatedOral200 mg
CapsuleOral100 mg/1
CapsuleOral200 mg/1
CapsuleOral50 mg/1
CapsuleOral100.000 mg
TabletOral100.000 mg
CapsuleOral200 mg
CapsuleOral100 mg
Prices
Unit descriptionCostUnit
Danazol powder21.42USD g
Danazol 200 mg capsule5.2USD capsule
Danocrine 200 mg capsule4.53USD capsule
Danazol 100 mg capsule2.92USD capsule
Cyclomen 200 mg Capsule2.31USD capsule
Danazol 50 mg capsule1.95USD capsule
Cyclomen 100 mg Capsule1.45USD capsule
Cyclomen 50 mg Capsule0.98USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)224.2-226.8Clinton, R. and Hanson, A.; US. Patent 3,135,743; June 2, 1964; assigned to Sterling Drug.
logP0.51PERRISSOUD,D & TESTA,B (1986)
Predicted Properties
PropertyValueSource
Water Solubility0.0176 mg/mLALOGPS
logP3.62ALOGPS
logP3.46Chemaxon
logS-4.3ALOGPS
pKa (Strongest Acidic)17.59Chemaxon
pKa (Strongest Basic)0.25Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area46.26 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity98.54 m3·mol-1Chemaxon
Polarizability38.44 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9781
Caco-2 permeable+0.8866
P-glycoprotein substrateSubstrate0.5938
P-glycoprotein inhibitor INon-inhibitor0.5194
P-glycoprotein inhibitor IINon-inhibitor0.8893
Renal organic cation transporterNon-inhibitor0.8178
CYP450 2C9 substrateNon-substrate0.8487
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.67
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.7407
CYP450 2D6 inhibitorNon-inhibitor0.8731
CYP450 2C19 inhibitorInhibitor0.5962
CYP450 3A4 inhibitorInhibitor0.796
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7692
Ames testNon AMES toxic0.6885
CarcinogenicityNon-carcinogens0.9083
BiodegradationNot ready biodegradable0.9562
Rat acute toxicity1.3291 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6896
hERG inhibition (predictor II)Non-inhibitor0.8734
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0ab9-0669000000-7afc135d5b1e92134191
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-000i-0009000000-9e745b8feecd354f6618
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-01b9-6902000000-854476472755ef5419e5
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-0006-9100000000-0d62c0c1b53c1cea5a25
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-0329000000-56adc37fd83dfa3c686f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-05ia-3931000000-1490f6c4984a84016076
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0009000000-3832c081e18b7f5bce6d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0009000000-e64f2bf50378cd01c2c6
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dr-0594000000-3e063f38f4b7c6071bd1
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0009000000-30ae8609b68e96aed398
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0bt9-0029000000-f342a81b84f446435611
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udr-0962000000-a834917ec1ff5203d115
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-187.390272
predicted
DarkChem Lite v0.1.0
[M-H]-187.042872
predicted
DarkChem Lite v0.1.0
[M-H]-191.179472
predicted
DarkChem Lite v0.1.0
[M-H]-176.58781
predicted
DeepCCS 1.0 (2019)
[M+H]+188.441372
predicted
DarkChem Lite v0.1.0
[M+H]+189.141172
predicted
DarkChem Lite v0.1.0
[M+H]+191.793272
predicted
DarkChem Lite v0.1.0
[M+H]+178.48323
predicted
DeepCCS 1.0 (2019)
[M+Na]+186.566972
predicted
DarkChem Lite v0.1.0
[M+Na]+187.191972
predicted
DarkChem Lite v0.1.0
[M+Na]+191.591772
predicted
DarkChem Lite v0.1.0
[M+Na]+184.26115
predicted
DeepCCS 1.0 (2019)

Targets

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Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
Molecular Weight
66215.45 Da
References
  1. Fujimoto J, Hori M, Itoh T, Ichigo S, Nishigaki M, Tamaya T: Danazol decreases transcription of estrogen receptor gene in human monocytes. Gen Pharmacol. 1995 May;26(3):507-16. [Article]
  2. Snyder BW, Beecham GD, Winneker RC: Danazol suppression of luteinizing hormone in the rat: evidence for mediation by both androgen and estrogen receptors. Proc Soc Exp Biol Med. 1990 May;194(1):54-7. [Article]
  3. Sanfilippo JS, Barrows GH, Apkarian RP, Wittliff JL: Evaluation of danazol influence upon the uterus using scanning electron microscopic morphometric and biochemical analyses. Surg Gynecol Obstet. 1985 May;160(5):421-8. [Article]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
Molecular Weight
98987.9 Da
References
  1. Donaldson VH: Danazol. Am J Med. 1989 Sep;87(3N):49N-55N. [Article]
  2. Sasagawa S, Shimizu Y, Kami H, Takeuchi T, Mita S, Imada K, Kato S, Mizuguchi K: Dienogest is a selective progesterone receptor agonist in transactivation analysis with potent oral endometrial activity due to its efficient pharmacokinetic profile. Steroids. 2008 Feb;73(2):222-31. Epub 2007 Oct 22. [Article]
  3. Gomez F, Ruiz P, Lopez R, Rivera C, Romero S, Bernal JA: Effects of androgen treatment on expression of macrophage Fcgamma receptors. Clin Diagn Lab Immunol. 2000 Jul;7(4):682-6. [Article]
  4. Roselli CE: The effect of anabolic-androgenic steroids on aromatase activity and androgen receptor binding in the rat preoptic area. Brain Res. 1998 May 11;792(2):271-6. [Article]
  5. Dmowski WP: Danazol. A synthetic steroid with diverse biologic effects. J Reprod Med. 1990 Jan;35(1 Suppl):69-74; discussion 74-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor ...
Gene Name
PGR
Uniprot ID
P06401
Uniprot Name
Progesterone receptor
Molecular Weight
98979.96 Da
References
  1. Beaumont H, Augood C, Duckitt K, Lethaby A: Danazol for heavy menstrual bleeding. Cochrane Database Syst Rev. 2007 Jul 18;(3):CD001017. [Article]
  2. Sasagawa S, Shimizu Y, Kami H, Takeuchi T, Mita S, Imada K, Kato S, Mizuguchi K: Dienogest is a selective progesterone receptor agonist in transactivation analysis with potent oral endometrial activity due to its efficient pharmacokinetic profile. Steroids. 2008 Feb;73(2):222-31. Epub 2007 Oct 22. [Article]
  3. Huang HF, Wang M: [Effects of gossypol acetate, danazol, progesterone and GnRH-A on estrogen and progesterone receptors of human endometrial cells]. Zhongguo Zhong Xi Yi Jie He Za Zhi. 1994 Jun;14(6):352-3, 325. [Article]
  4. Dmowski WP: Danazol. A synthetic steroid with diverse biologic effects. J Reprod Med. 1990 Jan;35(1 Suppl):69-74; discussion 74-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Negative modulator
General Function
Peptide binding
Specific Function
Receptor for gonadotropin releasing hormone (GnRH) that mediates the action of GnRH to stimulate the secretion of the gonadotropic hormones luteinizing hormone (LH) and follicle-stimulating hormone...
Gene Name
GNRHR
Uniprot ID
P30968
Uniprot Name
Gonadotropin-releasing hormone receptor
Molecular Weight
37730.355 Da
References
  1. Tian ZZ, Zhao H, Chen BY: [Effect of Chinese herbal medicine for nourishing yin and purging fire on mRNA expressions of gonadotropin-releasing hormone and its receptor in precocious puberty model rats]. Zhongguo Zhong Xi Yi Jie He Za Zhi. 2003 Sep;23(9):695-8. [Article]
  2. Menon M, Peegel H, Katta V: Inhibition of gonadotropin-releasing hormone receptors in rat anterior pituitary monolayer cell cultures by danazol. Am J Obstet Gynecol. 1986 Feb;154(2):367-72. [Article]
  3. Roth C, Hegemann F, Hildebrandt J, Balzer I, Witt A, Wuttke W, Jarry H: Pituitary and gonadal effects of GnRH (gonadotropin releasing hormone) analogues in two peripubertal female rat models. Pediatr Res. 2004 Jan;55(1):126-33. Epub 2003 Nov 6. [Article]
  4. Dmowski WP: Danazol. A synthetic steroid with diverse biologic effects. J Reprod Med. 1990 Jan;35(1 Suppl):69-74; discussion 74-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Negative modulator
General Function
Gonadotropin-releasing hormone receptor activity
Specific Function
Putative receptor for gonadotropin releasing hormone II (GnRH II) which is most probably non-functional.
Gene Name
GNRHR2
Uniprot ID
Q96P88
Uniprot Name
Putative gonadotropin-releasing hormone II receptor
Molecular Weight
32536.935 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Dmowski WP: Danazol. A synthetic steroid with diverse biologic effects. J Reprod Med. 1990 Jan;35(1 Suppl):69-74; discussion 74-5. [Article]
  4. Menon M, Peegel H, Katta V: Inhibition of gonadotropin-releasing hormone receptors in rat anterior pituitary monolayer cell cultures by danazol. Am J Obstet Gynecol. 1986 Feb;154(2):367-72. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Not Available
Specific Function
Not Available
Gene Name
CCL2
Uniprot ID
P13500
Uniprot Name
C-C motif chemokine 2
Molecular Weight
11024.87 Da
References
  1. Boucher A, Lemay A, Akoum A: Effect of hormonal agents on monocyte chemotactic protein-1 expression by endometrial epithelial cells of women with endometriosis. Fertil Steril. 2000 Nov;74(5):969-75. [Article]
  2. Jolicoeur C, Lemay A, Akoum A: Comparative effect of danazol and a GnRH agonist on monocyte chemotactic protein-1 expression by endometriotic cells. Am J Reprod Immunol. 2001 Feb;45(2):86-93. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Spina E, Pisani F, Perucca E: Clinically significant pharmacokinetic drug interactions with carbamazepine. An update. Clin Pharmacokinet. 1996 Sep;31(3):198-214. doi: 10.2165/00003088-199631030-00004. [Article]
  2. Zocor PI monograph [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxygen binding
Specific Function
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name
CYP19A1
Uniprot ID
P11511
Uniprot Name
Aromatase
Molecular Weight
57882.48 Da
References
  1. Murakami K, Nomura K, Shinohara K, Kasai T, Shozu M, Inoue M: Danazol inhibits aromatase activity of endometriosis-derived stromal cells by a competitive mechanism. Fertil Steril. 2006 Aug;86(2):291-7. doi: 10.1016/j.fertnstert.2005.12.074. Epub 2006 Jun 27. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Antagonist
General Function
Androgen binding
Specific Function
Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone...
Gene Name
SHBG
Uniprot ID
P04278
Uniprot Name
Sex hormone-binding globulin
Molecular Weight
43778.755 Da
References
  1. De Leo V, Morgante G, La Marca A, Musacchio MC, Sorace M, Cavicchioli C, Petraglia F: A benefit-risk assessment of medical treatment for uterine leiomyomas. Drug Saf. 2002;25(11):759-79. [Article]
  2. Telimaa S, Apter D, Reinila M, Ronnberg L, Kauppila A: Placebo-controlled comparison of hormonal and biochemical effects of danazol and high-dose medroxyprogesterone acetate. Eur J Obstet Gynecol Reprod Biol. 1990 Jul-Aug;36(1-2):97-105. [Article]
  3. Donaldson VH: Danazol. Am J Med. 1989 Sep;87(3N):49N-55N. [Article]
  4. Valimaki M, Nilsson CG, Roine R, Ylikorkala O: Comparison between the effects of nafarelin and danazol on serum lipids and lipoproteins in patients with endometriosis. J Clin Endocrinol Metab. 1989 Dec;69(6):1097-103. [Article]
  5. Forbes KL, Dowsett M, Rose GL, Mudge JE, Jeffcoate SL: Dosage-related effects of danazol on sex hormone binding globulin and free and total androgen levels. Clin Endocrinol (Oxf). 1986 Nov;25(5):597-605. [Article]

Drug created at July 13, 2007 20:36 / Updated at March 18, 2024 16:48