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Details

Stereochemistry ACHIRAL
Molecular Formula C2H6O3S2
Molecular Weight 142.1995
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2-MERCAPTOETHANESULFONIC ACID

SMILES

C(CS(=O)(=O)O)S

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

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

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL733: 4-Hydroxyifosfamide
Conditions

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
Detoxification of urotoxic oxazaphosphorines by sulfhydryl compounds.
1981
Prevention of urinary bladder tumors in cyclophosphamide-treated rats by additional medication with the uroprotectors sodium 2-mercaptoethane sulfonate (mesna) and disodium 2,2'-dithio-bis-ethane sulfonate (dimesna).
1983 Feb 15
Encephalopathy associated with ifosphamide/mesna therapy.
1985 Feb 16
Ifosfamide/mesa and encephalopathy.
1985 Mar 30
Cause and prevention of mafosfamide-induced venous pain.
1986
Ifosfamide plus mesna with and without adriamycin in soft tissue sarcoma.
1986
Avoiding ifosfamide/mesna encephalopathy.
1986 Aug 16
The protective effect of 2-mercapto-ethane sulfonate (MESNA) on hemorrhagic cystitis induced by high-dose ifosfamide treatment tested by a randomized crossover trial.
1986 Jun
Phase II study of ifosfamide in cervical cancer.
1986 Jun
Electron microscopic investigations of the cyclophosphamide-induced lesions of the urinary bladder of the rat and their prevention by mesna.
1987
Ifosfamide-induced subclinical tubular nephrotoxicity despite mesna.
1987 Feb
Efficacy of mesna in preventing further cyclophosphamide-induced hemorrhagic cystitis.
1988
Ifosfamide with mesna uroprotection in the management of lung cancer.
1990 Apr
[Ifosfamide-induced urinary bladder lesion and its inhibition by mesna].
1990 Aug
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
Allergic reactions to mesna.
1991 Aug 10
Allergic reactions to mesna.
1991 Sep 14
Comparison of N-acetylcysteine and mesna as uroprotectors with ifosfamide combination chemotherapy in refractory germ cell tumors.
1992 Aug
Mesna side effects which imitate vasculitis.
1992 Aug
Ifosfamide encephalopathy and methylene-blue: a case report.
1996 Aug
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
U.S. Food and Drug Administration drug approval summaries: imatinib mesylate, mesna tablets, and zoledronic acid.
2002
Pelvic primitive neuroectodermal tumor associated with a cluster of small round cell tumors: case report and review of current literature.
2003 Oct
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
Comparison of uroprotective efficacy of mesna and amifostine in Cyclophosphamide- induced hemorrhagic cystitis in rats.
2006 Jan-Mar
Ifosfamide metabolites CAA, 4-OH-Ifo and Ifo-mustard reduce apical phosphate transport by changing NaPi-IIa in OK cells.
2006 Nov
Histological changes in bladders of patients submitted to ifosfamide chemotherapy even with mesna prophylaxis.
2007 Apr
Acrolein and chloroacetaldehyde: an examination of the cell and cell-free biomarkers of toxicity.
2013 Feb 25
Surface functionalities of gold nanoparticles impact embryonic gene expression responses.
2013 Mar
Comparision of uroprotective activity of reduced glutathione with mesna in ifosfamide induced hemorrhagic cystitis in rats.
2014 Jan-Feb
The cytogenetic action of ifosfamide, mesna, and their combination on peripheral rabbit lymphocytes: an in vivo/in vitro cytogenetic study.
2014 Oct
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
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 Jun 25 22:41:47 UTC 2021 , Edited by admin on Fri Jun 25 22:41:47 UTC 2021
Code System Code Type Description
WIKIPEDIA
Mercaptoethanesulfonic acid
Created by admin on Fri Jun 25 22:41:47 UTC 2021 , Edited by admin on Fri Jun 25 22:41:47 UTC 2021
PRIMARY
FDA UNII
VHD28S0H7F
Created by admin on Fri Jun 25 22:41:47 UTC 2021 , Edited by admin on Fri Jun 25 22:41:47 UTC 2021
PRIMARY
EVMPD
SUB32737
Created by admin on Fri Jun 25 22:41:47 UTC 2021 , Edited by admin on Fri Jun 25 22:41:47 UTC 2021
PRIMARY
EPA CompTox
3375-50-6
Created by admin on Fri Jun 25 22:41:47 UTC 2021 , Edited by admin on Fri Jun 25 22:41:47 UTC 2021
PRIMARY
ECHA (EC/EINECS)
222-167-0
Created by admin on Fri Jun 25 22:41:47 UTC 2021 , Edited by admin on Fri Jun 25 22:41:47 UTC 2021
PRIMARY
PUBCHEM
598
Created by admin on Fri Jun 25 22:41:47 UTC 2021 , Edited by admin on Fri Jun 25 22:41:47 UTC 2021
PRIMARY
CAS
3375-50-6
Created by admin on Fri Jun 25 22:41:47 UTC 2021 , Edited by admin on Fri Jun 25 22:41:47 UTC 2021
PRIMARY
RXCUI
1546354
Created by admin on Fri Jun 25 22:41:47 UTC 2021 , Edited by admin on Fri Jun 25 22:41:47 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB09110
Created by admin on Fri Jun 25 22:41:47 UTC 2021 , Edited by admin on Fri Jun 25 22:41:47 UTC 2021
PRIMARY