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Details

Stereochemistry MIXED
Molecular Formula C12H6O12S6Sb2.6Na
Molecular Weight 916.017
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SODIUM STIBOCAPTATE

SMILES

[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[O-]C(=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=AOGOCZMBIYQOFE-UHFFFAOYSA-B
InChI=1S/3C4H6O4S2.6Na.2Sb/c3*5-3(6)1(9)2(10)4(7)8;;;;;;;;/h3*1-2,9-10H,(H,5,6)(H,7,8);;;;;;;;/q;;;6*+1;2*+3/p-12

HIDE SMILES / InChI
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

Curator's Comment: Succimer doesn't cross the blood-brain barrier in humans.

Originator

Sources: Dermatologische Wochenschrift (1954), 129, (20), 497-500. 

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
CHEMET

Approved Use

For the treatment of lead poisoning in pediatric patients with blood lead levels above 45 ug/dL.

Launch Date

1993
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
25.3 μM
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
318 μM × h
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2 day
single, oral
SUCCIMER blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
9.9 h
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
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

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
weak
PubMed

PubMed

TitleDatePubMed
Anti microbial activity of dimercaptosuccinic acid (DMSA): a new chelating agent.
2001 Dec
[Ambulatory treatment for lead poisoning].
2002 Aug
Lipoic acid in combination with a chelator ameliorates lead-induced peroxidative damages in rat kidney.
2002 Aug
Mercury toxicity and antioxidants: Part 1: role of glutathione and alpha-lipoic acid in the treatment of mercury toxicity.
2002 Dec
Effect of meso-2,3-dimercaptosuccinic acid on urinary lead excretion in exposed men.
2002 Nov
The renal Na(+)-dependent dicarboxylate transporter, NaDC-3, translocates dimethyl- and disulfhydryl-compounds and contributes to renal heavy metal detoxification.
2002 Nov
Haematological, hepatic and renal alterations after repeated oral or intraperitoneal administration of monoisoamyl DMSA. I. Changes in male rats.
2002 Nov-Dec
Do children with falling blood lead levels have improved cognition?
2002 Oct
Reversal of lead-induced oxidative stress by chelating agent, antioxidant, or their combination in the rat.
2002 Sep
[Managing childhood lead poisoning].
2003
Arsenic uptake by native fern species in Thailand: effect of chelating agents on hyperaccumulation of arsenic by Pityrogramma calomelanos.
2003
Vitamin C, glutathione, or lipoic acid did not decrease brain or kidney mercury in rats exposed to mercury vapor.
2003
[Metal poisoning].
2003
A patient with postoperative mercury contamination of the peritoneum.
2003
Dimercaptosuccinic acid and Prussian Blue in the treatment of acute thallium poisoning in rats.
2003
Acute arsenic poisoning treated by intravenous dimercaptosuccinic acid (DMSA) and combined extrarenal epuration techniques.
2003
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
Acute pyelonephritis and sequelae of renal scar in pediatric first febrile urinary tract infection.
2003 Apr
Comparison of relative renal function by renal scintigraphy and lateralized creatinine clearance in children with bilateral vesicoureteral reflux.
2003 Apr
One-pot preparation of subnanometer-sized gold clusters via reduction and stabilization by meso-2,3-dimercaptosuccinic acid.
2003 Apr 9
Succimer (meso-2,3-dimercaptosuccinic acid (DMSA)) treatment of Andean children with environmental lead exposure.
2003 Apr-Jun
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
Studies of urinary cystine precipitation in vitro: ontogeny of cystine nephrolithiasis and identification of meso-2,3-dimercaptosuccinic acid as a potential therapy for cystinuria.
2003 Dec
Interaction between metals and chelating agents affects glutamate binding on brain synaptic membranes.
2003 Dec
Reversal of cadmium induced oxidative stress by chelating agent, antioxidant or their combination in rat.
2003 Dec 10
Functional evaluation by quantitative dimercaptosuccinic Acid scintigraphy after kidney trauma in children.
2003 Feb
The efficacy of monoisoamyl ester of dimercaptosuccinic acid in chronic experimental arsenic poisoning in mice.
2003 Jan
Chronic arsenic toxicity: clinical features, epidemiology, and treatment: experience in West Bengal.
2003 Jan
Severe lead poisoning in pregnancy.
2003 Jan-Feb
Subcutaneous injection of metallic mercury.
2003 Jun
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
Metal chelators change the human sperm motility pattern.
2003 Jun
Beneficial effect of combined administration of some naturally occurring antioxidants (vitamins) and thiol chelators in the treatment of chronic lead intoxication.
2003 Jun 15
Oral treatment of avian lead intoxication with meso-2,3-dimercaptosuccinic acid.
2003 Mar
The role of oxidative stress in the in vitro induction of micronuclei by pesticides in mouse lung fibroblasts.
2003 Mar
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
Haematological, hepatic and renal alterations after repeated oral and intraperitoneal administration of monoisoamyl DMSA. II. Changes in female rats.
2003 Mar-Apr
Interaction of dimercaptosuccinic acid (DMSA) with angiotensin II on calcium mobilization in vascular smooth muscle cells.
2003 May 15
Successful ways to increase retention in a longitudinal study of lead-exposed children.
2003 Nov
Ascorbic acid supplementation does not improve efficacy of meso-dimercaptosuccinic acid treatment in lead-exposed suckling rats.
2003 Oct
Gunshot-induced plumbism in an adult male.
2003 Oct
Lead toxicosis in cats-a review.
2003 Oct
Analysis of meso-2,3-dimercaptosuccinic acid in human urine by capillary electrophoresis using direct injection.
2003 Oct
Effect of succimer on growth of preschool children with moderate blood lead levels.
2004 Feb
Resistive index in febrile urinary tract infections: predictive value of renal outcome.
2004 Feb
Ultrasonography in the evaluation of renal scarring using DMSA scan as the gold standard.
2004 Feb
Therapeutic potential of monoisoamyl and monomethyl esters of meso 2,3-dimercaptosuccinic acid in gallium arsenide intoxicated rats.
2004 Feb 15
Combined efficacies of lipoic acid and 2,3-dimercaptosuccinic acid against lead-induced lipid peroxidation in rat liver.
2004 Jan
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
Reductions in blood lead overestimate reductions in brain lead following repeated succimer regimens in a rodent model of childhood lead exposure.
2004 Mar

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Succimer is given as injection (MPI DMSA KIDNEY REAGENT product).
10 mg/kg or 350 mg/m2 every eight hours for five days
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
SODIUM STIBOCAPTATE
INN   MART.  
INN  
Official Name English
TWSB
Code English
RO-4-1544-6
Code English
STIBOCAPTATE SODIUM
Common Name English
HEXASODIUM SALT OF THE S,S-DIESTER OF THE CYCLIC THIOANTIMONATE(III) OF 2,3-DIMERCAPTOSUCCINIC ACID
Common Name English
STIBOCAPTATE [MI]
Common Name English
RO 4-1544-6
Code English
SODIUM STIBOCAPTATE [MART.]
Common Name English
TWS-B
Code English
sodium stibocaptate [INN]
Common Name English
Code System Code Type Description
SMS_ID
100000083552
Created by admin on Fri Dec 15 15:00:22 GMT 2023 , Edited by admin on Fri Dec 15 15:00:22 GMT 2023
PRIMARY
PUBCHEM
18293
Created by admin on Fri Dec 15 15:00:22 GMT 2023 , Edited by admin on Fri Dec 15 15:00:22 GMT 2023
PRIMARY
CAS
3064-61-7
Created by admin on Fri Dec 15 15:00:22 GMT 2023 , Edited by admin on Fri Dec 15 15:00:22 GMT 2023
PRIMARY
EVMPD
SUB10570MIG
Created by admin on Fri Dec 15 15:00:22 GMT 2023 , Edited by admin on Fri Dec 15 15:00:22 GMT 2023
PRIMARY
NCI_THESAURUS
C152379
Created by admin on Fri Dec 15 15:00:22 GMT 2023 , Edited by admin on Fri Dec 15 15:00:22 GMT 2023
PRIMARY
INN
2001
Created by admin on Fri Dec 15 15:00:22 GMT 2023 , Edited by admin on Fri Dec 15 15:00:22 GMT 2023
PRIMARY
FDA UNII
VFV49ULL8Q
Created by admin on Fri Dec 15 15:00:22 GMT 2023 , Edited by admin on Fri Dec 15 15:00:22 GMT 2023
PRIMARY
MERCK INDEX
m10211
Created by admin on Fri Dec 15 15:00:22 GMT 2023 , Edited by admin on Fri Dec 15 15:00:22 GMT 2023
PRIMARY Merck Index