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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

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

1988
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
[High-dose ifosfamide therapy: systemic use of a mucolytic agent for the reduction of urotoxicity].
1979 Dec 8
Detoxification of urotoxic oxazaphosphorines by sulfhydryl compounds.
1981
Treatment of ifosfamide-induced urothelial toxicity by oral administration of sodium 2-mercaptoethane sulphonate (MESNA) to patients with inoperable lung cancer.
1983 Feb
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
Experience with mesna in patients receiving allogeneic bone marrow transplants for poor prognostic leukaemia.
1983 Sep
[Prevention of tumor formation in the bladder by sodium-2-mercaptoethane sulfonate (mesna). Experimental studies and clinical consequences].
1984 Sep
Ifosfamide/mesa and encephalopathy.
1985 Mar 30
Phase II trial of ifosfamide with mesna in previously treated metastatic sarcoma.
1985 May
Ifosfamide plus mesna with and without adriamycin in soft tissue sarcoma.
1986
CNS-side effects induced by Ifosfamide-Mesna in children with osteosarcomas.
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
Blurring of vision due to ifosfamide.
1987
Ifosfamide/mesna encephalopathy.
1987 Apr 25
Irreversible encephalopathy with ifosfamide/mesna.
1987 Aug
Ifosfamide-induced subclinical tubular nephrotoxicity despite mesna.
1987 Feb
Encephalopathy with rapid infusion ifosfamide/mesna.
1987 Feb 14
Ifosfamide neurotoxicity in children.
1987 Mar
Ifosfamide/mesna related encephalopathy: a case report with a possible role of phenobarbital in enhancing neurotoxicity.
1988
[Encephalopathy caused by an ifosfamide-mesna combination].
1988 Apr 2
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
Mesna versus hyperhydration for the prevention of cyclophosphamide-induced hemorrhagic cystitis in bone marrow transplantation.
1991 Nov
Response of cyclophosphamide-resistant Wegener's granulomatosis to etoposide.
1992 Aug 15
Ifosfamide encephalopathy and methylene-blue: a case report.
1996 Aug
Continuous subcutaneous administration of mesna to prevent ifosfamide-induced hemorrhagic cystitis.
1996 Jun
Combined intravenous and oral mesna in outpatients treated with ifosfamide.
1997
Influence of mesna on urotoxic effects of selected bromosubstituted analogs of ifosfamide.
1997
Pharmacological and histopathological study of cyclophosphamide-induced hemorrhagic cystitis - comparison of the effects of dexamethasone and Mesna.
1999 Oct
Prevention of further cyclophosphamide induced hemorrhagic cystitis by hyperbaric oxygen and mesna in guinea pigs.
2001 Sep
Hyperbaric oxygen therapy for cyclophosphamide induced refractory hemorrhagic cystitis in a child.
2004 Aug
Contribution of flavonoid antioxidants to the preventive effect of mesna in cyclophosphamide-induced cystitis in rats.
2005 Aug
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
A 50-year-old man with burkitt lymphoma.
2008 Oct
Surface functionalities of gold nanoparticles impact embryonic gene expression responses.
2013 Mar
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 Dec 15 15:58:56 GMT 2023 , Edited by admin on Fri Dec 15 15:58:56 GMT 2023
Code System Code Type Description
WIKIPEDIA
Mercaptoethanesulfonic acid
Created by admin on Fri Dec 15 15:58:56 GMT 2023 , Edited by admin on Fri Dec 15 15:58:56 GMT 2023
PRIMARY
FDA UNII
VHD28S0H7F
Created by admin on Fri Dec 15 15:58:56 GMT 2023 , Edited by admin on Fri Dec 15 15:58:56 GMT 2023
PRIMARY
EVMPD
SUB32737
Created by admin on Fri Dec 15 15:58:56 GMT 2023 , Edited by admin on Fri Dec 15 15:58:56 GMT 2023
PRIMARY
DAILYMED
VHD28S0H7F
Created by admin on Fri Dec 15 15:58:56 GMT 2023 , Edited by admin on Fri Dec 15 15:58:56 GMT 2023
PRIMARY
CHEBI
17905
Created by admin on Fri Dec 15 15:58:56 GMT 2023 , Edited by admin on Fri Dec 15 15:58:56 GMT 2023
PRIMARY
CHEBI
58319
Created by admin on Fri Dec 15 15:58:56 GMT 2023 , Edited by admin on Fri Dec 15 15:58:56 GMT 2023
PRIMARY
EPA CompTox
DTXSID8023264
Created by admin on Fri Dec 15 15:58:56 GMT 2023 , Edited by admin on Fri Dec 15 15:58:56 GMT 2023
PRIMARY
SMS_ID
100000126313
Created by admin on Fri Dec 15 15:58:56 GMT 2023 , Edited by admin on Fri Dec 15 15:58:56 GMT 2023
PRIMARY
ECHA (EC/EINECS)
222-167-0
Created by admin on Fri Dec 15 15:58:56 GMT 2023 , Edited by admin on Fri Dec 15 15:58:56 GMT 2023
PRIMARY
PUBCHEM
598
Created by admin on Fri Dec 15 15:58:56 GMT 2023 , Edited by admin on Fri Dec 15 15:58:56 GMT 2023
PRIMARY
CAS
3375-50-6
Created by admin on Fri Dec 15 15:58:56 GMT 2023 , Edited by admin on Fri Dec 15 15:58:56 GMT 2023
PRIMARY
RXCUI
1546354
Created by admin on Fri Dec 15 15:58:56 GMT 2023 , Edited by admin on Fri Dec 15 15:58:56 GMT 2023
PRIMARY RxNorm
DRUG BANK
DB09110
Created by admin on Fri Dec 15 15:58:56 GMT 2023 , Edited by admin on Fri Dec 15 15:58:56 GMT 2023
PRIMARY