Thiosulfuric acid

Identification

Summary

Thiosulfuric acid is a sulfur donor used for sequential use with sodium nitrite for the reversal of acute cyanide poisoning that is judged to be life-threatening.

Brand Names
Nithiodote, Seacalphyx
Generic Name
Thiosulfuric acid
DrugBank Accession Number
DB09499
Background

Thiosulfuric acid (as sodium thiosulfate) has the chemical name thiosulfuric acid, disodium salt, pentahydrate. The chemical formula is Na2S2O3•5H2O and the molecular weight is 248.17. Sodium Thiosulfate Injection is a cyanide antidote which contains one 50 mL glass vial containing a 25% solution of Sodium Thiosulfate Injection.

It has been indicated as antidote for cyanide poisoning. It is also used as adjunct agent for patients taking cisplatin chemotherapy.

Beside the above indications, sodium thiosulfate could be used as ingredient in the following: agricultural chemicals (non-pesticidal), fillers, intermediates, laboratory chemicals, oxidizing/reducing agents, process regulators, processing aids, and solids separation agents.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 114.144
Monoisotopic: 113.94453531
Chemical Formula
H2O3S2
Synonyms
  • Monosulfanemonosulfonic acid
  • Sulfurothioic S-acid

Pharmacology

Indication

Indicated for sequential intravenous use with sodium nitrite for the treatment of acute cyanide poisoning that is judged to be life-threatening.

Pharmacology
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Associated Conditions
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Contraindications
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Pharmacodynamics

In dogs, pretreatment with sodium thiosulfate to achieve a steady state level of 2 µmol/mL increased the rate of conversion of cyanide to thiocyanate over 30-fold.

Mechanism of action

As antidote: Sodium thiosulfate acts as a sulfur donor for the endogenous sulfur transferase enzyme, rhodanese. It is used together with sodium nitrite for cyanide poisiong as antidote. Cyanide has a very high affinity for iron in the ferric state. It reacts with the trivalent (ferric) iron of mitochondrial cytochrome oxidase, thereby inhibiting cellular respiration, resulting in lactic acidosis and cytotoxic hypoxia. Sodium nitrite reacts with hemoglobin to form methemoglobin, which competes with cytochrome oxidase for the cyanide ion. Cyanide binds to methemoglobin to form cyanmethemoglobin and restore the activity of cytochrome oxidase. When cyanide dissociates from methemoglobin, sodium thiosulfate facilitates its conversion by rhodanese to thiocyanate, a less toxic ion. As antineoplastic adjunct: The mechanism of action of sodium thiosulfate is still not clear, but it is thought that it forms a complex with cisplastin via covalent bond, which renders cisplastin more readily eliminated from the kidneys. It was believed also that sodium thiosulfate plays a role in the protection from nephrotoxicity caused by cisplastin, through reducing delivery of cisplatin to the kidneys and by neutralizing cisplatin in the kidneys where sodium thiosulfate is highly concentrated.

Absorption

Thiosulfate taken orally is not systemically absorbed. Most of the thiosulfate is oxidized to sulfate or is incorporated into endogenous sulphur compounds; a small proportion is excreted through the kidneys. After an intravenous injection of 1 g sodium thiosulfate in patients, the reported serum thiosulfate half-life was approximately 20 minutes. However, after an intravenous injection of a substantially higher dose of sodium thiosulfate (150 mg/kg, that is, 9 g for 60 kg body weight) in normal healthy men, the reported elimination half-life was 182 minutes.

Volume of distribution

150 mL/kg.

Protein binding

Data not found.

Metabolism

Data not found.

Route of elimination

Elimination is primarily renal, approximately 20-50% of exogenously administered thiosulfate is eliminated unchanged via the kidneys Antidote (to cyanide poisoning): Primarily as thiocyanate. Antineoplastic adjunct: As a nontoxic sodium thiosulfate/cisplatin complex.

Half-life

Thiosulfate: 15 to 20 minutes.

Clearance

1.86 ± 0.45 ml/min per kg.

Adverse Effects
Adverseeffects
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Toxicity

Oral, rat : LD50 = >5000mg/kg

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
Technetium Tc-99m oxidronateThiosulfuric acid may decrease effectiveness of Technetium Tc-99m oxidronate as a diagnostic agent.
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Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Sodium thiosulfateL0IYT1O31N7772-98-7AKHNMLFCWUSKQB-UHFFFAOYSA-L
Sodium thiosulfate pentahydrateHX1032V43M10102-17-7PODWXQQNRWNDGD-UHFFFAOYSA-L
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
SeacalphyxSolution250 mg / mLIntravenousSeaford Pharmaceuticals Inc2013-01-08Not applicableCanada flag
Sodium ThiosulfateInjection, solution250 mg/1mLIntravenousHope Pharmaceuticals2012-02-14Not applicableUS flag
Sodium Thiosulfate Inj 25% USPLiquid250 mg / mLIntravenousDavid Bull Laboratories (Pty) Ltd.1991-12-311998-08-13Canada flag
Sodium Thiosulfate Injection USPSolution250 mg / mLIntravenousHope Pharmaceuticals2015-11-23Not applicableCanada flag
Sodium Thiosulfate Injection USPSolution250 mg / mLIntravenousPfizer Canada Ulc1998-07-13Not applicableCanada flag
Sodum ThiosulfateInjection, solution100 mg/1mLIntravenousAmerican Regent1990-09-302012-11-28US flag
Sodum ThiosulfateInjection, solution250 mg/1mLIntravenousAmerican Regent1990-09-302012-11-28US flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Oligostim SoufreTablet0.015 mgOralDolisos Laboratoires S.A.1998-06-112007-08-01Canada flag
วีเนียPowder15 gบริษัท วิทยาศรม จำกัด1991-10-18Not applicableThailand flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Adasept Acne GelSodium thiosulfate (8 %) + Salicylic acid (2 %) + Triclosan (0.5 %)LotionTopicalOdan Laboratories Ltd1974-12-31Not applicableCanada flag
NithiodoteSodium thiosulfate pentahydrate (250 mg/1mL) + Sodium nitrite (30 mg/1mL)IntravenousHope Pharmaceuticals2011-01-14Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Sodium polysulthionate and folic acidSodium thiosulfate pentahydrate (1.8 mg/1) + Folic acid (1 mg/1) + Octasulfur (388 mg/1) + Sodium sulfate decahydrate (8 mg/1)CapsuleOralSolubiomix2016-08-242017-10-16US flag
Sodium polysulthionate, 5-methyltetrahydrofolateSodium thiosulfate pentahydrate (.45 g/100g) + Levomefolic acid (.125 g/100g) + Octasulfur (97 g/100g) + Sodium sulfate decahydrate (2 g/100g)PowderOral; TopicalSolubiomix2015-07-212016-01-12US flag
Sodium Polysulthionate, 5-mthfSodium thiosulfate pentahydrate (1.8 mg/1) + 5-methyltetrahydrofolic acid (.5 mg/1) + Octasulfur (388 mg/1) + Sodium sulfate decahydrate (8 mg/1)CapsuleOralSolubiomix2016-01-092016-01-12US flag
Sodum ThiosulfateSodium thiosulfate pentahydrate (100 mg/1mL)Injection, solutionIntravenousAmerican Regent1990-09-302012-11-28US flag
Sodum ThiosulfateSodium thiosulfate pentahydrate (250 mg/1mL)Injection, solutionIntravenousAmerican Regent1990-09-302012-11-28US flag
XizflusSodium thiosulfate pentahydrate (.45 g/100g) + 5-methyltetrahydrofolic acid (.125 g/100g) + Octasulfur (97 g/100g) + Sodium sulfate decahydrate (2 g/100g)PowderOral; TopicalBasiem2015-07-142016-01-12US flag
XizflusSodium thiosulfate pentahydrate (1.8 mg/1) + 5-methyltetrahydrofolic acid (.5 mg/1) + Octasulfur (388 mg/1) + Sodium sulfate decahydrate (8 mg/1)CapsuleOralBasiem2016-01-092016-01-12US flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of inorganic compounds known as non-metal thiosulfates. These are inorganic non-metallic compounds containing a thiosulfate as its largest oxoanion.
Kingdom
Inorganic compounds
Super Class
Homogeneous non-metal compounds
Class
Non-metal oxoanionic compounds
Sub Class
Non-metal thiosulfates
Direct Parent
Non-metal thiosulfates
Alternative Parents
Inorganic sulfides / Inorganic oxides
Substituents
Inorganic oxide / Inorganic sulfide / Non-metal thiosulfate
Molecular Framework
Not Available
External Descriptors
thiosulfuric acid (CHEBI:29279)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
7K79Y2EKKP
CAS number
13686-28-7
InChI Key
DHCDFWKWKRSZHF-UHFFFAOYSA-N
InChI
InChI=1S/H2O3S2/c1-5(2,3)4/h(H2,1,2,3,4)
IUPAC Name
dihydroxy-1λ⁶-disulfen-1-one
SMILES
OS(O)(=O)=S

References

General References
  1. MSDS [Link]
  2. Monograph [Link]
  3. product info [Link]
  4. product info [Link]
  5. database [Link]
Human Metabolome Database
HMDB0060293
KEGG Compound
C05529
PubChem Compound
24478
PubChem Substance
347827866
ChemSpider
22886
ChEBI
29279
ChEMBL
CHEMBL1208642
ZINC
ZINC000008214573
Wikipedia
Thiosulfuric_acid

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4TerminatedTreatmentCutaneous calcification1
3CompletedSupportive CareChildhood Germ Cell Tumor / Extragonadal Germ Cell Tumor / Liver Cancer / Neoplasms, Brain / Neuroblastoma (NB) / Ototoxicity / Ovarian Cancer / Sarcomas / Tumors of the Central Nervous System1
3CompletedTreatmentLiver Cancer / Ototoxicity1
3RecruitingTreatmentCalciphylaxis1
3RecruitingTreatmentHepatoblastomas1
3TerminatedTreatmentCalcific Uremic Arteriolopathy (CUA) / Calciphylaxis1
3TerminatedTreatmentCalciphylaxis1
2Active Not RecruitingPreventionHeart Failure / Myocardial Infarction1
2Active Not RecruitingSupportive CareClinical Stage III Human Papillomavirus (HPV)-Mediated (p16-Positive) Oropharyngeal Carcinoma AJCC v8 / Clinical Stage IV HPV-Mediated (p16-Positive) Oropharyngeal Carcinoma AJCC v8 / Locally Advanced Head and Neck Squamous Cell Carcinoma / Locally Advanced Hypopharyngeal Squamous Cell Carcinoma / Locally Advanced Laryngeal Squamous Cell Carcinoma / Locally Advanced Oral Cavity Squamous Cell Carcinoma / Locally Advanced Oropharyngeal Squamous Cell Carcinoma / Pathologic Stage III HPV-Mediated (p16-Positive) Oropharyngeal Carcinoma AJCC v8 / Pathologic Stage IV HPV-Mediated (p16-Positive) Oropharyngeal Carcinoma AJCC v8 / Stage III Hypopharyngeal Carcinoma AJCC v8 / Stage III Laryngeal Cancer AJCC v8 / Stage III Lip and Oral Cavity Cancer AJCC v8 / Stage III Oropharyngeal (p16-Negative) Carcinoma AJCC v8 / Stage IV Hypopharyngeal Carcinoma AJCC v8 / Stage IV Laryngeal Cancer AJCC v8 / Stage IV Lip and Oral Cavity Cancer AJCC v8 / Stage IV Oropharyngeal (p16-Negative) Carcinoma AJCC v8 / Stage IVA Hypopharyngeal Carcinoma AJCC v8 / Stage IVA Laryngeal Cancer AJCC v8 / Stage IVA Lip and Oral Cavity Cancer AJCC v8 / Stage IVA Oropharyngeal (p16-Negative) Carcinoma AJCC v8 / Stage IVB Hypopharyngeal Carcinoma AJCC v8 / Stage IVB Laryngeal Cancer AJCC v8 / Stage IVB Lip and Oral Cavity Cancer AJCC v8 / Stage IVB Oropharyngeal (p16-Negative) Carcinoma AJCC v8 / Stage IVC Hypopharyngeal Carcinoma AJCC v8 / Stage IVC Laryngeal Cancer AJCC v8 / Stage IVC Lip and Oral Cavity Cancer AJCC v8 / Stage IVC Oropharyngeal (p16-Negative) Carcinoma AJCC v81
2Active Not RecruitingTreatmentGliomas, Malignant1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
LotionTopical
TabletOral0.015 mg
SolutionIntravenous250 mg / mL
Injection, solution, concentrateIntravenous
LiquidIntravenous250 mg / mL
Injection, solutionIntravenous100 mg/1mL
Injection, solutionIntravenous250 mg/1mL
PowderOral
SolutionIntravenous200 mg
CapsuleOral
PowderOral; Topical
Powder15 g
Injection, solutionIntravenous262.5 mg/1ml
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US8496973No2013-07-302031-03-29US flag
US8568793No2013-10-292031-12-24US flag
US9585912No2017-03-072031-03-29US flag
US9345724No2016-05-242031-03-29US flag

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
logP0.048ChemAxon
pKa (Strongest Acidic)11.35ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity21.76 m3·mol-1ChemAxon
Polarizability8.51 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-2900000000-cfd5e2fee5605aa6f365
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-1900000000-14f35b6955762fa5ef9c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01pk-9300000000-6d71fc2acfdc5c953636
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-4fefeb50f8b5131bb095
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-1900000000-25562aa85ac0e34c2f5b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-1900000000-c55a98b5b4d32b24a3cd

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Substrate
General Function
Thiosulfate sulfurtransferase activity
Specific Function
Formation of iron-sulfur complexes, cyanide detoxification or modification of sulfur-containing enzymes. Other thiol compounds, besides cyanide, can act as sulfur ion acceptors. Also has weak merca...
Gene Name
TST
Uniprot ID
Q16762
Uniprot Name
Thiosulfate sulfurtransferase
Molecular Weight
33428.69 Da

Drug created on November 30, 2015 19:10 / Updated on September 28, 2021 07:54