GOSSYPOL, (R)-

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C30H30O8
Molecular Weight	518.5544
Optical Activity	NONE
Additional Stereochemistry	Yes
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0
Stereo Comments	AXIAL, R

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)C1=C(O)C(O)=C(C=O)C2=C(O)C(=C(C)C=C12)C3=C(O)C4=C(C=C3C)C(C(C)C)=C(O)C(O)=C4C=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

Molecular Formula	C30H30O8
Molecular Weight	518.5544
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.drugs.com/npp/gossypol.html
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Protein kinase C (PKC) 44 Target ID: CHEMBL2093867 Sources: http://www.bioscreening.net/glossary/gossypol/	Inhibitor 8297
Calcineurin 3 Target ID: Calcineurin Sources: https://www.ncbi.nlm.nih.gov/pubmed/17141216	Inhibitor 8297	14.2 µM [IC50]
Inositol-trisphosphate 3-kinase A 1 Target ID: P23677 Gene ID: 3706.0 Gene Symbol: ITPKA Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15659385	Inhibitor 8297	115.0 nM [IC50]
Inositol-trisphosphate 3-kinase B 1 Target ID: P27987 Gene ID: 3707.0 Gene Symbol: ITPKB Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15659385	Inhibitor 8297	340.0 nM [IC50]
Inositol polyphosphate multikinase 1 Target ID: Q8NFU5 Gene ID: 253430.0 Gene Symbol: IPMK Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15659385	Inhibitor 8297	3.4 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Pregnancy 65 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12020773	Preventing	Phase III 656	Unknown Approved Use Unknown
Adrenocortical carcinoma 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7544429	Primary	Phase II 1132	Unknown Approved Use Unknown
Glioblastoma multiforme 30 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24968413	Primary	Phase II 1132	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Screening for new compounds with antiherpes activity.	1984 Oct	6517562
Monkey lactate dehydrogenase-C4 as a model for the interaction of enzymes with gossypol.	1986 Jun	3769483
Selective inhibition of human immunodeficiency virus type 1 replication by the (-) but not the (+) enantiomer of gossypol.	1989 Dec	2619282
Inactivation of human immunodeficiency virus in vitro by gossypol.	1989 Jun	2473865
Inhibition of human immunodeficiency virus type I replication by derivatives of gossypol.	1991 Dec	1805194
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.	1991 Jan-Feb	1710653
Profile of capsaicin-induced mouse ear oedema as neurogenic inflammatory model: comparison with arachidonic acid-induced ear oedema.	1993 Dec	7508328
Anti-HIV-1 activity and cellular pharmacology of various analogs of gossypol.	1993 Jul 20	8347147
Comparative in vitro study of contraceptive agents with anti-HIV activity: gramicidin, nonoxynol-9, and gossypol.	1994 Feb	7511493
Synthesis and anti-HIV activity of 1,1'-dideoxygossypol and related compounds.	1995 Jun 23	7608907
Gossypol as a male antifertility agent--why studies should have been continued.	1998 Feb	9639145
Low dose gossypol for male contraception.	2000 Dec	11202417
Gossypol and gossypolone enantiomers in tissues of rainbow trout fed low and high levels of dietary cottonseed meal.	2002 May 8	11982441
Type of cottonseed and level of gossypol in diets of lactating dairy cows: plasma gossypol, health, and reproductive performance.	2003 Mar	12703626
Effect of gossypol in association with chromium protoporphyrin on heme metabolic enzymes.	2004 Feb	15027808
Sertoli cell junctional proteins as early targets for different classes of reproductive toxicants.	2004 May	15082077
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	15451339
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	16020667
A fluorescence-based coupling reaction for monitoring the activity of recombinant human NAD synthetase.	2005 Oct	16305310
-(-)Gossypol promotes the apoptosis of bladder cancer cells in vitro.	2008 Nov-Dec	18840529
Combined gossypol and zoledronic acid treatment results in synergistic induction of cell death and regulates angiogenic molecules in ovarian cancer cells.	2009 Sep	19825521
Inhibition of lactate dehydrogenase A induces oxidative stress and inhibits tumor progression.	2010 Feb 2	20133848
The pan-Bcl-2 inhibitor (-)-gossypol triggers autophagic cell death in malignant glioma.	2010 Jul	20587533
Mirabamides E-H, HIV-inhibitory depsipeptides from the sponge Stelletta clavosa.	2011 Feb 25	21280591
Discovery of N-hydroxyindole-based inhibitors of human lactate dehydrogenase isoform A (LDH-A) as starvation agents against cancer cells.	2011 Mar 24	21332213
Towards a systematic analysis of human short-chain dehydrogenases/reductases (SDR): Ligand identification and structure-activity relationships.	2015 Jun 5	25526675

Patents

Sample Use Guides

In Vivo Use Guide

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:42:48 GMT 2023` Edited by `admin` on `Fri Dec 15 15:42:48 GMT 2023`
Record UNII	8DY2X8LXW4
Record Status	`Validated (UNII)`
Record Version

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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