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Details

Stereochemistry ACHIRAL
Molecular Formula C2H6O3S2
Molecular Weight 142.197
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2-MERCAPTOETHANESULFONIC ACID

SMILES

OS(=O)(=O)CCS

InChI

InChIKey=ZNEWHQLOPFWXOF-UHFFFAOYSA-N
InChI=1S/C2H6O3S2/c3-7(4,5)2-1-6/h6H,1-2H2,(H,3,4,5)

HIDE SMILES / InChI

Molecular Formula C2H6O3S2
Molecular Weight 142.197
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8c79a07d-32cc-4fe7-9a74-152c169f1c4f http://www.drugbank.ca/drugs/DB09110 https://en.wikipedia.org/wiki/Mesna

Mesna is an organosulfur compound used as an adjuvant in cancer chemotherapy involving cyclophosphamide and ifosfamide. No clinical drug interaction studies have been conducted with mesna. Mesna concentrates in the bladder where acrolein accumulates after administration of chemotherapy and through a Michael addition, forms a conjugate with acrolein and other urotoxic metabolites. This conjugation reaction inactivates the urotoxic compounds to harmless metabolites. The most common adverse reactions (> 10%) when MESNEX is given with ifosfamide are nausea, vomiting, constipation, leukopenia, fatigue, fever, anorexia, thrombocytopenia, anemia, granulocytopenia, diarrhea, asthenia, abdominal pain, headache, alopecia, and somnolence.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
MESNEX

Approved Use

Mesna Injection is indicated as a prophylactic agent in reducing the incidence of ifosfamide-induced hemorrhagic cystitis. Limitation of Use: Mesna Injection is not indicated to reduce the risk of hematuria due to other pathological conditions such as thrombocytopenia. Mesna Injection is a cytoprotective agent indicated as a prophylactic agent in reducing the incidence of ifosfamide-induced hemorrhagic cystitis. (1) Limitation of Use: Mesna Injection is not indicated to reduce the risk of hematuria due to other pathological conditions such as thrombocytopenia. (1)

Launch Date

5.9944318E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
33 μM
1.2 g single, oral
dose: 1.2 g
route of administration: Oral
experiment type: SINGLE
co-administered:
MESNA blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
511 μM
1.2 g single, intravenous
dose: 1.2 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
MESNA blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
79 μM
0.24 g/m² single, intravenous
dose: 0.24 g/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
MESNA blood
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
110 μM × h
1.2 g single, oral
dose: 1.2 g
route of administration: Oral
experiment type: SINGLE
co-administered:
MESNA blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
201 μM × h
1.2 g single, intravenous
dose: 1.2 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
MESNA blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
49 μM × h
0.24 g/m² single, intravenous
dose: 0.24 g/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
MESNA blood
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
92 min
0.24 g/m² single, intravenous
dose: 0.24 g/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
MESNA blood
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1200 mg single, intravenous
Highest studied dose
Dose: 1200 mg
Route: intravenous
Route: single
Dose: 1200 mg
Sources:
healthy
n = 16
Other AEs: Headache, Hypoaesthesia...
Other AEs:
Headache (43.8%)
Hypoaesthesia (0%)
Malaise (0%)
Myalgia (0%)
Nausea (0%)
Pharyngitis (0%)
Somnolence (6.3%)
Upper respiratory infection (0%)
Vomiting (0%)
Dizziness (6.3%)
Abdominal pain (6.3%)
Coughing (0%)
Diarrhea (6.3%)
Anorexia (0%)
Flushing (12.5%)
Injection site reaction (12.5%)
Back pain (6.3%)
Dyspepsia (12.5%)
Paraesthesia (6.3%)
Renal pain (6.3%)
Rigors (12.5%)
Fatigue (0%)
Conjunctivitis (6.3%)
Arthralgia (12.5%)
Application site reaction (31.3%)
Photophobia (18.8%)
Dehydration (6.3%)
Dysuria (6.3%)
Sweating increased (6.3%)
Sources:
2400 mg single, oral
Highest studied dose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
healthy
n = 12
Other AEs: Headache, Hypoaesthesia...
Other AEs:
Headache (33.3%)
Hypoaesthesia (0%)
Malaise (8.3%)
Myalgia (0%)
Nausea (16.7%)
Pharyngitis (0%)
Somnolence (8.3%)
Upper respiratory infection (0%)
Vomiting (16.7%)
Dizziness (8.3%)
Abdominal pain (8.3%)
Coughing (0%)
Diarrhea (0%)
Anorexia (8.3%)
Flushing (0%)
Injection site reaction (0%)
Back pain (0%)
Dyspepsia (0%)
Paraesthesia (8.3%)
Renal pain (0%)
Rigors (0%)
Fatigue (8.3%)
Conjunctivitis (0%)
Arthralgia (0%)
Application site reaction (0%)
Photophobia (0%)
Dehydration (0%)
Dysuria (0%)
Sweating increased (0%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Anorexia 0%
1200 mg single, intravenous
Highest studied dose
Dose: 1200 mg
Route: intravenous
Route: single
Dose: 1200 mg
Sources:
healthy
n = 16
Coughing 0%
1200 mg single, intravenous
Highest studied dose
Dose: 1200 mg
Route: intravenous
Route: single
Dose: 1200 mg
Sources:
healthy
n = 16
Fatigue 0%
1200 mg single, intravenous
Highest studied dose
Dose: 1200 mg
Route: intravenous
Route: single
Dose: 1200 mg
Sources:
healthy
n = 16
Hypoaesthesia 0%
1200 mg single, intravenous
Highest studied dose
Dose: 1200 mg
Route: intravenous
Route: single
Dose: 1200 mg
Sources:
healthy
n = 16
Malaise 0%
1200 mg single, intravenous
Highest studied dose
Dose: 1200 mg
Route: intravenous
Route: single
Dose: 1200 mg
Sources:
healthy
n = 16
Myalgia 0%
1200 mg single, intravenous
Highest studied dose
Dose: 1200 mg
Route: intravenous
Route: single
Dose: 1200 mg
Sources:
healthy
n = 16
Nausea 0%
1200 mg single, intravenous
Highest studied dose
Dose: 1200 mg
Route: intravenous
Route: single
Dose: 1200 mg
Sources:
healthy
n = 16
Pharyngitis 0%
1200 mg single, intravenous
Highest studied dose
Dose: 1200 mg
Route: intravenous
Route: single
Dose: 1200 mg
Sources:
healthy
n = 16
Upper respiratory infection 0%
1200 mg single, intravenous
Highest studied dose
Dose: 1200 mg
Route: intravenous
Route: single
Dose: 1200 mg
Sources:
healthy
n = 16
Vomiting 0%
1200 mg single, intravenous
Highest studied dose
Dose: 1200 mg
Route: intravenous
Route: single
Dose: 1200 mg
Sources:
healthy
n = 16
Arthralgia 12.5%
1200 mg single, intravenous
Highest studied dose
Dose: 1200 mg
Route: intravenous
Route: single
Dose: 1200 mg
Sources:
healthy
n = 16
Dyspepsia 12.5%
1200 mg single, intravenous
Highest studied dose
Dose: 1200 mg
Route: intravenous
Route: single
Dose: 1200 mg
Sources:
healthy
n = 16
Flushing 12.5%
1200 mg single, intravenous
Highest studied dose
Dose: 1200 mg
Route: intravenous
Route: single
Dose: 1200 mg
Sources:
healthy
n = 16
Injection site reaction 12.5%
1200 mg single, intravenous
Highest studied dose
Dose: 1200 mg
Route: intravenous
Route: single
Dose: 1200 mg
Sources:
healthy
n = 16
Rigors 12.5%
1200 mg single, intravenous
Highest studied dose
Dose: 1200 mg
Route: intravenous
Route: single
Dose: 1200 mg
Sources:
healthy
n = 16
Photophobia 18.8%
1200 mg single, intravenous
Highest studied dose
Dose: 1200 mg
Route: intravenous
Route: single
Dose: 1200 mg
Sources:
healthy
n = 16
Application site reaction 31.3%
1200 mg single, intravenous
Highest studied dose
Dose: 1200 mg
Route: intravenous
Route: single
Dose: 1200 mg
Sources:
healthy
n = 16
Headache 43.8%
1200 mg single, intravenous
Highest studied dose
Dose: 1200 mg
Route: intravenous
Route: single
Dose: 1200 mg
Sources:
healthy
n = 16
Abdominal pain 6.3%
1200 mg single, intravenous
Highest studied dose
Dose: 1200 mg
Route: intravenous
Route: single
Dose: 1200 mg
Sources:
healthy
n = 16
Back pain 6.3%
1200 mg single, intravenous
Highest studied dose
Dose: 1200 mg
Route: intravenous
Route: single
Dose: 1200 mg
Sources:
healthy
n = 16
Conjunctivitis 6.3%
1200 mg single, intravenous
Highest studied dose
Dose: 1200 mg
Route: intravenous
Route: single
Dose: 1200 mg
Sources:
healthy
n = 16
Dehydration 6.3%
1200 mg single, intravenous
Highest studied dose
Dose: 1200 mg
Route: intravenous
Route: single
Dose: 1200 mg
Sources:
healthy
n = 16
Diarrhea 6.3%
1200 mg single, intravenous
Highest studied dose
Dose: 1200 mg
Route: intravenous
Route: single
Dose: 1200 mg
Sources:
healthy
n = 16
Dizziness 6.3%
1200 mg single, intravenous
Highest studied dose
Dose: 1200 mg
Route: intravenous
Route: single
Dose: 1200 mg
Sources:
healthy
n = 16
Dysuria 6.3%
1200 mg single, intravenous
Highest studied dose
Dose: 1200 mg
Route: intravenous
Route: single
Dose: 1200 mg
Sources:
healthy
n = 16
Paraesthesia 6.3%
1200 mg single, intravenous
Highest studied dose
Dose: 1200 mg
Route: intravenous
Route: single
Dose: 1200 mg
Sources:
healthy
n = 16
Renal pain 6.3%
1200 mg single, intravenous
Highest studied dose
Dose: 1200 mg
Route: intravenous
Route: single
Dose: 1200 mg
Sources:
healthy
n = 16
Somnolence 6.3%
1200 mg single, intravenous
Highest studied dose
Dose: 1200 mg
Route: intravenous
Route: single
Dose: 1200 mg
Sources:
healthy
n = 16
Sweating increased 6.3%
1200 mg single, intravenous
Highest studied dose
Dose: 1200 mg
Route: intravenous
Route: single
Dose: 1200 mg
Sources:
healthy
n = 16
Application site reaction 0%
2400 mg single, oral
Highest studied dose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
healthy
n = 12
Arthralgia 0%
2400 mg single, oral
Highest studied dose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
healthy
n = 12
Back pain 0%
2400 mg single, oral
Highest studied dose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
healthy
n = 12
Conjunctivitis 0%
2400 mg single, oral
Highest studied dose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
healthy
n = 12
Coughing 0%
2400 mg single, oral
Highest studied dose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
healthy
n = 12
Dehydration 0%
2400 mg single, oral
Highest studied dose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
healthy
n = 12
Diarrhea 0%
2400 mg single, oral
Highest studied dose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
healthy
n = 12
Dyspepsia 0%
2400 mg single, oral
Highest studied dose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
healthy
n = 12
Dysuria 0%
2400 mg single, oral
Highest studied dose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
healthy
n = 12
Flushing 0%
2400 mg single, oral
Highest studied dose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
healthy
n = 12
Hypoaesthesia 0%
2400 mg single, oral
Highest studied dose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
healthy
n = 12
Injection site reaction 0%
2400 mg single, oral
Highest studied dose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
healthy
n = 12
Myalgia 0%
2400 mg single, oral
Highest studied dose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
healthy
n = 12
Pharyngitis 0%
2400 mg single, oral
Highest studied dose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
healthy
n = 12
Photophobia 0%
2400 mg single, oral
Highest studied dose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
healthy
n = 12
Renal pain 0%
2400 mg single, oral
Highest studied dose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
healthy
n = 12
Rigors 0%
2400 mg single, oral
Highest studied dose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
healthy
n = 12
Sweating increased 0%
2400 mg single, oral
Highest studied dose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
healthy
n = 12
Upper respiratory infection 0%
2400 mg single, oral
Highest studied dose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
healthy
n = 12
Nausea 16.7%
2400 mg single, oral
Highest studied dose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
healthy
n = 12
Vomiting 16.7%
2400 mg single, oral
Highest studied dose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
healthy
n = 12
Headache 33.3%
2400 mg single, oral
Highest studied dose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
healthy
n = 12
Abdominal pain 8.3%
2400 mg single, oral
Highest studied dose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
healthy
n = 12
Anorexia 8.3%
2400 mg single, oral
Highest studied dose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
healthy
n = 12
Dizziness 8.3%
2400 mg single, oral
Highest studied dose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
healthy
n = 12
Fatigue 8.3%
2400 mg single, oral
Highest studied dose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
healthy
n = 12
Malaise 8.3%
2400 mg single, oral
Highest studied dose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
healthy
n = 12
Paraesthesia 8.3%
2400 mg single, oral
Highest studied dose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
healthy
n = 12
Somnolence 8.3%
2400 mg single, oral
Highest studied dose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
healthy
n = 12
PubMed

PubMed

TitleDatePubMed
Prevention of isophosphamide-induced urothelial toxicity with 2-mercaptoethane sulphonate sodium (mesnum) in patients with advanced carcinoma.
1980 Sep 27
Phase II trial of ifosfamide with mesna in previously treated metastatic sarcoma.
1985 May
Central nervous system toxicity following the treatment of pediatric patients with ifosfamide/mesna.
1986 Aug
Avoiding ifosfamide/mesna encephalopathy.
1986 Aug 16
Blurring of vision due to ifosfamide.
1987
Irreversible encephalopathy with ifosfamide/mesna.
1987 Aug
Encephalopathy with rapid infusion ifosfamide/mesna.
1987 Feb 14
Chloroacetaldehyde and its contribution to urotoxicity during treatment with cyclophosphamide or ifosfamide. An experimental study/short communication.
1989 Jun
Dana-Farber Cancer Institute studies in advanced sarcoma.
1990 Feb
Placebo-controlled double-blind comparative study on the preventive efficacy of mesna against ifosfamide-induced urinary disorders.
1991
Mesna versus hyperhydration for the prevention of cyclophosphamide-induced hemorrhagic cystitis in bone marrow transplantation.
1991 Nov
Ifosfamide with mesna in squamous carcinoma of the cervix: phase II results in patients with advanced or recurrent disease.
1991 Nov
Primary tumour mutant p53 gene protein and epidermal growth factor receptor expression and doxorubicin plus ifosfamide for recurrent breast cancer.
1992 Mar
Encephalopathy in ifosfamide-treated patients.
1992 Nov
Oral ifosfamide-mesna: a clinical investigation in advanced non-small-cell lung cancer.
1992 Nov
[Epileptic seizures and treatment with ifosfamide-mesna].
1994
Prevention of cyclophosphamide-induced hemorrhagic cystitis by glucose-mannose binding plant lectins.
1999 Jun
Pharmacological and histopathological study of cyclophosphamide-induced hemorrhagic cystitis - comparison of the effects of dexamethasone and Mesna.
1999 Oct
[Hemorrhagic cystitis related to the high-dose conditioning therapy in a bone marrow recipient].
2001
DICE (dexamethasone, ifosfamide, cisplatin, etoposide) infusional chemotherapy for refractory or relapsed non-Hodgkin's lymphoma (NHL).
2001 Jul
Use of dexamethasone with mesna for the prevention of ifosfamide-induced hemorrhagic cystitis.
2003 Nov
Pelvic primitive neuroectodermal tumor associated with a cluster of small round cell tumors: case report and review of current literature.
2003 Oct
Outcome after hyperbaric oxygen treatment for cyclophosphamide-induced refractory hemorrhagic cystitis.
2003 Sep
Hyperbaric oxygen therapy for cyclophosphamide induced refractory hemorrhagic cystitis in a child.
2004 Aug
Ternatin, a flavonoid, prevents cyclophosphamide and ifosfamide-induced hemorrhagic cystitis in rats.
2004 Feb
Contribution of antioxidants to preventive effect of mesna in cyclophosphamide-induced hemorrhagic cystitis in rats.
2004 Nov
A 50-year-old man with burkitt lymphoma.
2008 Oct
Acrolein and chloroacetaldehyde: an examination of the cell and cell-free biomarkers of toxicity.
2013 Feb 25
Patents

Sample Use Guides

240 mg/m2 every 4 hours (injection) or 240 mg/m2 (first point, injection) following with 480 mg/m2 (2 and 6 hours, oral).
Route of Administration: Other
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:58:56 UTC 2023
Edited
by admin
on Fri Dec 15 15:58:56 UTC 2023
Record UNII
VHD28S0H7F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
2-MERCAPTOETHANESULFONIC ACID
Systematic Name English
MESNA FREE ACID
Common Name English
.BETA.-MERCAPTOETHANESULFONIC ACID
Systematic Name English
COENZYME M
Common Name English
MERCAPTOETHANESULFONIC ACID
Systematic Name English
Classification Tree Code System Code
NDF-RT N0000180854
Created by admin on Fri Dec 15 15:58:56 UTC 2023 , Edited by admin on Fri Dec 15 15:58:56 UTC 2023
Code System Code Type Description
WIKIPEDIA
Mercaptoethanesulfonic acid
Created by admin on Fri Dec 15 15:58:56 UTC 2023 , Edited by admin on Fri Dec 15 15:58:56 UTC 2023
PRIMARY
FDA UNII
VHD28S0H7F
Created by admin on Fri Dec 15 15:58:56 UTC 2023 , Edited by admin on Fri Dec 15 15:58:56 UTC 2023
PRIMARY
EVMPD
SUB32737
Created by admin on Fri Dec 15 15:58:56 UTC 2023 , Edited by admin on Fri Dec 15 15:58:56 UTC 2023
PRIMARY
DAILYMED
VHD28S0H7F
Created by admin on Fri Dec 15 15:58:56 UTC 2023 , Edited by admin on Fri Dec 15 15:58:56 UTC 2023
PRIMARY
CHEBI
17905
Created by admin on Fri Dec 15 15:58:56 UTC 2023 , Edited by admin on Fri Dec 15 15:58:56 UTC 2023
PRIMARY
CHEBI
58319
Created by admin on Fri Dec 15 15:58:56 UTC 2023 , Edited by admin on Fri Dec 15 15:58:56 UTC 2023
PRIMARY
EPA CompTox
DTXSID8023264
Created by admin on Fri Dec 15 15:58:56 UTC 2023 , Edited by admin on Fri Dec 15 15:58:56 UTC 2023
PRIMARY
SMS_ID
100000126313
Created by admin on Fri Dec 15 15:58:56 UTC 2023 , Edited by admin on Fri Dec 15 15:58:56 UTC 2023
PRIMARY
ECHA (EC/EINECS)
222-167-0
Created by admin on Fri Dec 15 15:58:56 UTC 2023 , Edited by admin on Fri Dec 15 15:58:56 UTC 2023
PRIMARY
PUBCHEM
598
Created by admin on Fri Dec 15 15:58:56 UTC 2023 , Edited by admin on Fri Dec 15 15:58:56 UTC 2023
PRIMARY
CAS
3375-50-6
Created by admin on Fri Dec 15 15:58:56 UTC 2023 , Edited by admin on Fri Dec 15 15:58:56 UTC 2023
PRIMARY
RXCUI
1546354
Created by admin on Fri Dec 15 15:58:56 UTC 2023 , Edited by admin on Fri Dec 15 15:58:56 UTC 2023
PRIMARY RxNorm
DRUG BANK
DB09110
Created by admin on Fri Dec 15 15:58:56 UTC 2023 , Edited by admin on Fri Dec 15 15:58:56 UTC 2023
PRIMARY
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