STIBOCAPTATE

Details

Stereochemistry	MIXED
Molecular Formula	C12H12O12S6Sb2
Molecular Weight	784.126
Optical Activity	UNSPECIFIED
Defined Stereocenters	0 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)C(S[Sb]1SC(C(S1)C(O)=O)C(O)=O)C(S[Sb]2SC(C(S2)C(O)=O)C(O)=O)C(O)=O

InChI

InChIKey=WRIDGMJGKDWAJY-UHFFFAOYSA-H

InChI=1S/3C4H6O4S2.2Sb/c3*5-3(6)1(9)2(10)4(7)8;;/h3*1-2,9-10H,(H,5,6)(H,7,8);;/q;;;2*+3/p-6

HIDE SMILES / InChI

Molecular Formula	C12H12O12S6Sb2
Molecular Weight	784.126
Charge	0
Count

Stereochemistry	MIXED
Additional Stereochemistry	No
Defined Stereocenters	0 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.who.int/selection_medicines/committees/expert/18/applications/succimer.pdf

Succimer is an analogue of dimercaprol, and has replaced dimercaprol as one of the main antidotes used in the management of poisoning by lead and other heavy metals. The advantages of succimer are that it is effective by oral administration because it is soluble in water, it is well-tolerated, has relatively low toxicity and can be given at the same time as iron supplements to treat iron deficiency anaemia. It does not cause significant increase in urinary excretion of essential minerals unlike the other widelyused lead chelating agent, sodium calcium EDTA.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Lead 16 Target ID: CHEMBL2364029 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/019998s013lbl.pdf	Chelating Agent 142

Conditions

Condition	Modality	Targets	Highest Phase	Product
Lead poisoning in children 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/019998s013lbl.pdf	Curative		Approved 8429	CHEMET Approved Use For the treatment of lead poisoning in pediatric patients with blood lead levels above 45 ug/dL. Launch Date 1993

C_max

Value	Dose	Co-administered	Analyte	Population
25.3 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7716789/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		SUCCIMER plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
55 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7588486/	10 mg/kg bw single, oral dose: 10 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:		STIBOCAPTATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
318 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7716789/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		SUCCIMER plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
2 day DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/019998s013lbl.pdf	single, oral	SUCCIMER blood	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
9.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7716789/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	SUCCIMER plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
3.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7588486/	10 mg/kg bw single, oral dose: 10 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:	STIBOCAPTATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	OAT1 326

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
OAT1 326	substrate 3367 Sources: https://www.tandfonline.com/doi/full/10.1080/24734306.2020.1870077	weak

PubMed

Title	Date	PubMed
Anti microbial activity of dimercaptosuccinic acid (DMSA): a new chelating agent.	2001 Dec	12396095
[Ambulatory treatment for lead poisoning].	2002 Aug	12244800
Lipoic acid in combination with a chelator ameliorates lead-induced peroxidative damages in rat kidney.	2002 Aug	12185410
Lead induced oxidative damage and its response to combined administration of alpha-lipoic acid and succimers in rats.	2002 Aug 15	12135622
Severe congenital lead poisoning in a preterm infant due to a herbal remedy.	2002 Aug 19	12175323
Mercury toxicity and antioxidants: Part 1: role of glutathione and alpha-lipoic acid in the treatment of mercury toxicity.	2002 Dec	12495372
Acute renal damage in infants after first urinary tract infection.	2002 Jul	12172762
Reflux nephropathy in transplants.	2002 Jul	12172759
Procalcitonin as a marker of acute pyelonephritis in infants and children.	2002 Jun	12107804
Combined administration of oxalic acid, succimer and its analogue for the reversal of gallium arsenide-induced oxidative stress in rats.	2002 Jun	12107644
Effect of meso-2,3-dimercaptosuccinic acid on urinary lead excretion in exposed men.	2002 Nov	12507251
The renal Na(+)-dependent dicarboxylate transporter, NaDC-3, translocates dimethyl- and disulfhydryl-compounds and contributes to renal heavy metal detoxification.	2002 Nov	12397032
Haematological, hepatic and renal alterations after repeated oral or intraperitoneal administration of monoisoamyl DMSA. I. Changes in male rats.	2002 Nov-Dec	12424740
Do children with falling blood lead levels have improved cognition?	2002 Oct	12359796
Reversal of lead-induced oxidative stress by chelating agent, antioxidant, or their combination in the rat.	2002 Sep	12359191
[Managing childhood lead poisoning].	2003	14746008
Vitamin C, glutathione, or lipoic acid did not decrease brain or kidney mercury in rats exposed to mercury vapor.	2003	12870874
A patient with postoperative mercury contamination of the peritoneum.	2003	12733856
Dimercaptosuccinic acid and Prussian Blue in the treatment of acute thallium poisoning in rats.	2003	12733851
Acute arsenic poisoning treated by intravenous dimercaptosuccinic acid (DMSA) and combined extrarenal epuration techniques.	2003	12645960
Combined efficacies of lipoic acid and meso-2,3-dimercaptosuccinic acid on lead-induced erythrocyte membrane lipid peroxidation and antioxidant status in rats.	2003 Apr	12755469
Acute pyelonephritis and sequelae of renal scar in pediatric first febrile urinary tract infection.	2003 Apr	12700963
Comparison of relative renal function by renal scintigraphy and lateralized creatinine clearance in children with bilateral vesicoureteral reflux.	2003 Apr	12670571
One-pot preparation of subnanometer-sized gold clusters via reduction and stabilization by meso-2,3-dimercaptosuccinic acid.	2003 Apr 9	12670215
Succimer (meso-2,3-dimercaptosuccinic acid (DMSA)) treatment of Andean children with environmental lead exposure.	2003 Apr-Jun	12848245
Reverse of the differential uptake intensity of Tc-99m MIBI and Tc-99m V-DMSA by multiple myeloma lesions in response to therapy.	2003 Aug	12897645
Functional evaluation by quantitative dimercaptosuccinic Acid scintigraphy after kidney trauma in children.	2003 Feb	12544333
The efficacy of monoisoamyl ester of dimercaptosuccinic acid in chronic experimental arsenic poisoning in mice.	2003 Jan	12635830
Chronic arsenic toxicity: clinical features, epidemiology, and treatment: experience in West Bengal.	2003 Jan	12635824
Symposium on radionuclides in paediatric nephro-urology.	2003 Jan	12557855
Severe lead poisoning in pregnancy.	2003 Jan-Feb	12540252
Effects of calcium disodium EDTA and meso-2,3-dimercaptosuccinic acid on tissue concentrations of lead for use in treatment of calves with experimentally induced lead toxicosis.	2003 Jun	12828250
Beneficial effect of combined administration of some naturally occurring antioxidants (vitamins) and thiol chelators in the treatment of chronic lead intoxication.	2003 Jun 15	12732454
Oral treatment of avian lead intoxication with meso-2,3-dimercaptosuccinic acid.	2003 Mar	12723805
The role of oxidative stress in the in vitro induction of micronuclei by pesticides in mouse lung fibroblasts.	2003 Mar	12621067
Effects of dietary lead and/or dimercaptosuccinic acid exposure on regional serotonin and serotonin metabolite content in rainbow trout (Oncorhynchus mykiss).	2003 Mar 20	12614918
2,3-Dimercaptopropane-1-sulfonic acid and meso-2,3-dimercaptosuccinic acid increase mercury- and cadmium-induced inhibition of delta-aminolevulinate dehydratase.	2003 Mar 3	12499112
Haematological, hepatic and renal alterations after repeated oral and intraperitoneal administration of monoisoamyl DMSA. II. Changes in female rats.	2003 Mar-Apr	12666153
Interaction of dimercaptosuccinic acid (DMSA) with angiotensin II on calcium mobilization in vascular smooth muscle cells.	2003 May 15	12754110
Successful ways to increase retention in a longitudinal study of lead-exposed children.	2003 Nov	14679710
Ascorbic acid supplementation does not improve efficacy of meso-dimercaptosuccinic acid treatment in lead-exposed suckling rats.	2003 Oct	14629742
Gunshot-induced plumbism in an adult male.	2003 Oct	14620713
Lead toxicosis in cats-a review.	2003 Oct	12948499
Analysis of meso-2,3-dimercaptosuccinic acid in human urine by capillary electrophoresis using direct injection.	2003 Oct	12904952
Effect of succimer on growth of preschool children with moderate blood lead levels.	2004 Feb	14754579
Resistive index in febrile urinary tract infections: predictive value of renal outcome.	2004 Feb	14685837
Therapeutic potential of monoisoamyl and monomethyl esters of meso 2,3-dimercaptosuccinic acid in gallium arsenide intoxicated rats.	2004 Feb 15	14751669
Combined efficacies of lipoic acid and 2,3-dimercaptosuccinic acid against lead-induced lipid peroxidation in rat liver.	2004 Jan	14711456
2,3-Dimercaptopropanol, 2,3-dimercaptopropane-1-sulfonic acid, and meso-2,3-dimercaptosuccinic acid inhibit delta-aminolevulinate dehydratase from human erythrocytes in vitro.	2004 Mar	15016592
Reductions in blood lead overestimate reductions in brain lead following repeated succimer regimens in a rodent model of childhood lead exposure.	2004 Mar	14998744

Sample Use Guides

In Vivo Use Guide

10 mg/kg or 350 mg/m2 every eight hours for five days

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Sat Dec 16 18:05:49 GMT 2023` Edited by `admin` on `Sat Dec 16 18:05:49 GMT 2023`
Record UNII	9WCI9N7UUQ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

STIBOCAPTATE

Common Name

English

SUCCINIC ACID, 2,3-DIMERCAPTO-, CYCLIC THIOANTIMONATE(III), S,S-DIESTER WITH 2,3-DIMERCAPTOSUCCINIC ACID

Common Name

English

ASTIBAN ACID

Common Name

English

1,3,2-DITHIASTIBOLANE-4,5-DICARBOXYLIC ACID, 2,2'-((1,2-DICARBOXY-1,2-ETHANEDIYL)BIS(THIO))BIS-

Common Name

English

Code System Code Type Description

ECHA (EC/EINECS)

217-858-9