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Details

Stereochemistry ABSOLUTE
Molecular Formula C30H30O8
Molecular Weight 518.5555
Optical Activity NONE
Additional Stereochemistry Yes
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0
Stereo Comments AXIAL, R

SHOW SMILES / InChI
Structure of GOSSYPOL, (R)-

SMILES

CC(C)c1c2cc(C)c(-c3c(C)cc4c(C(C)C)c(c(c(C=O)c4c3O)O)O)c(c2c(C=O)c(c1O)O)O

InChI

InChIKey=QBKSWRVVCFFDOT-UHFFFAOYSA-N
InChI=1S/C30H30O8/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36/h7-12,33-38H,1-6H3

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/24073600 | http://www.webmd.com/vitamins-supplements/ingredientmono-106-gossypol.aspx?activeingredientid=106&activeingredientname=gossypol

Gossypol is a substance that is found in the cotton plant. It is removed from the seeds and used for medicine. Gossypol is effective as a nonhormonal male contraceptive; however, it has been documented to have irreversible effects on male fertility. Gossypol is reported to exhibit antioxidant, anticancer, antivirus, antiparasitic, and antimicrobial properties and lower plasma cholesterol. Nausea, emesis, anorexia, diarrhea, altered taste sensation, small intestine obstruction, and fatigue have been recorded in clinical trials as adverse reactions. Large amounts of gossypol can decrease potassium levels in the body. Low potassium levels can increase the side effects of digoxin.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Calcineurin
14.2 µM [IC50]
Target ID: P23677
Gene ID: 3706.0
Gene Symbol: ITPKA
Target Organism: Homo sapiens (Human)
115.0 nM [IC50]
Target ID: P27987
Gene ID: 3707.0
Gene Symbol: ITPKB
Target Organism: Homo sapiens (Human)
340.0 nM [IC50]
Target ID: Q8NFU5
Gene ID: 253430.0
Gene Symbol: IPMK
Target Organism: Homo sapiens (Human)
3.4 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Screening for new compounds with antiherpes activity.
1984 Oct
Monkey lactate dehydrogenase-C4 as a model for the interaction of enzymes with gossypol.
1986 Jun
Selective inhibition of human immunodeficiency virus type 1 replication by the (-) but not the (+) enantiomer of gossypol.
1989 Dec
Anti-HIV-1 activity and cellular pharmacology of various analogs of gossypol.
1993 Jul 20
Comparative in vitro study of contraceptive agents with anti-HIV activity: gramicidin, nonoxynol-9, and gossypol.
1994 Feb
Synthesis and anti-HIV activity of 1,1'-dideoxygossypol and related compounds.
1995 Jun 23
Gossypol as a male antifertility agent--why studies should have been continued.
1998 Feb
Type of cottonseed and level of gossypol in diets of lactating dairy cows: plasma gossypol, health, and reproductive performance.
2003 Mar
Effect of gossypol in association with chromium protoporphyrin on heme metabolic enzymes.
2004 Feb
Sertoli cell junctional proteins as early targets for different classes of reproductive toxicants.
2004 May
A combined regimen of gossypol plus methyltestosterone and ethinylestradiol as a contraceptive induces germ cell apoptosis and expression of its related genes in rats.
2004 Oct
Reversal of cisplatin resistance with a BH3 mimetic, (-)-gossypol, in head and neck cancer cells: role of wild-type p53 and Bcl-xL.
2005 Jul
Patents

Sample Use Guides

15 mg per day for 12 weeks or, if needed, for 16 weeks to reach spermatogenesis suppression.
Route of Administration: Oral
In Vitro Use Guide
In the testing of the possibility of the inactivation of HIV, it was found that a concentration of 100uM of gossypol completely inactivates cell-free preparations of HIV. Following exposure of cell-free incubates of HIV to 100 uM gossypol, ultracentrifugation and inoculation of the washed pellet onto H9 cells, there is no evidence of elevated reverse transcriptase activity over 21 days. Treatment with lower concentrations of gossypol reduces the peak and lengthens the time to maximal reverse transcriptase activity compared with control cultures.
Name Type Language
GOSSYPOL, (R)-
Common Name English
(R)-2,2'-BIS(8-FORMYL-1,6,7-TRIHYDROXY-5-ISOPROPYL-3-METHYLNAPHTHALENE)
Common Name English
(R)-GOSSYPOL
Common Name English
NSC-726190
Code English
GOSSYPOL R-FORM [MI]
Common Name English
GOSSYPOL, R-
Common Name English
(-)-GOSSYPOL
Common Name English
R-(-)-GOSSYPOL
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 230206
Created by admin on Fri Jun 25 21:56:45 UTC 2021 , Edited by admin on Fri Jun 25 21:56:45 UTC 2021
Code System Code Type Description
MERCK INDEX
M5834
Created by admin on Fri Jun 25 21:56:45 UTC 2021 , Edited by admin on Fri Jun 25 21:56:45 UTC 2021
PRIMARY Merck Index
FDA UNII
8DY2X8LXW4
Created by admin on Fri Jun 25 21:56:45 UTC 2021 , Edited by admin on Fri Jun 25 21:56:45 UTC 2021
PRIMARY
CAS
90141-22-3
Created by admin on Fri Jun 25 21:56:45 UTC 2021 , Edited by admin on Fri Jun 25 21:56:45 UTC 2021
PRIMARY