mesna Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
	1711	3375-50-6

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: mesna mercaptoethanesulfonic acid reduced coenzyme M	A sulfhydryl compound used to prevent urothelial toxicity by inactivating metabolites from ANTINEOPLASTIC AGENTS, such as IFOSFAMIDE or CYCLOPHOSPHAMIDE. Molecular weight: 142.19 Formula: C2H6O3S2 CLOGP: -1.55 LIPINSKI: 0 HAC: 3 HDO: 1 TPSA: 54.37 ALOGS: -1.05 ROTB: 2 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

mesna
mercaptoethanesulfonic acid
reduced coenzyme M

A sulfhydryl compound used to prevent urothelial toxicity by inactivating metabolites from ANTINEOPLASTIC AGENTS, such as IFOSFAMIDE or CYCLOPHOSPHAMIDE.

Molecular weight: 142.19
Formula: C2H6O3S2
CLOGP: -1.55
LIPINSKI: 0
HAC: 3
HDO: 1
TPSA: 54.37
ALOGS: -1.05
ROTB: 2

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
1.20	g	Inhal.solution

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	28.13 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	62 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	0.65 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	20.50 mL/min/kg	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	0.36 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
Dec. 30, 1988	FDA	BAXTER HLTHCARE

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Encephalopathy	395.73	24.04	161	7198	33428	46645275
Febrile neutropenia	362.91	24.04	210	7149	94417	46584286
Mucosal inflammation	217.14	24.04	111	7248	38865	46639838
Pancytopenia	133.45	24.04	109	7250	84949	46593754
Neutropenia	131.70	24.04	136	7223	143068	46535635
Cystitis haemorrhagic	106.30	24.04	34	7325	3513	46675190
Pyrexia	101.84	24.04	190	7169	348612	46330091
Febrile bone marrow aplasia	80.95	24.04	33	7326	6829	46671874
Neurotoxicity	78.97	24.04	40	7319	13677	46665026
Toxic encephalopathy	76.05	24.04	29	7330	5033	46673670
Cytomegalovirus infection	71.13	24.04	41	7318	18103	46660600
Haematotoxicity	67.22	24.04	29	7330	6904	46671799
Product use in unapproved indication	60.83	24.04	73	7286	90200	46588503
Thrombocytopenia	55.54	24.04	83	7276	126498	46552205
Leukopenia	52.26	24.04	59	7300	68284	46610419
Drug ineffective	47.48	24.04	24	7335	677814	46000889
Idiopathic pneumonia syndrome	41.46	24.04	10	7349	362	46678341
Off label use	40.97	24.04	142	7217	379699	46299004
Venoocclusive liver disease	38.66	24.04	17	7342	4234	46674469
Vena cava thrombosis	34.59	24.04	13	7346	2166	46676537
Bone marrow failure	34.27	24.04	32	7327	29637	46649066
BK polyomavirus test positive	34.19	24.04	6	7353	41	46678662
Hypokalaemia	33.37	24.04	54	7305	87970	46590733
Cytokine release syndrome	32.49	24.04	17	7342	6206	46672497
Sepsis	32.08	24.04	68	7291	135946	46542757
Cardiotoxicity	31.26	24.04	17	7342	6705	46671998
Mitral valve disease	30.82	24.04	12	7347	2200	46676503
Anaemia	30.49	24.04	99	7260	255680	46423023
Pneumothorax	29.96	24.04	22	7337	14607	46664096
Chronic hepatitis B	29.16	24.04	7	7352	248	46678455
Periorbital cellulitis	29.04	24.04	8	7351	492	46678211
Arthralgia	28.43	24.04	11	7348	364592	46314111
Blood phosphorus decreased	27.36	24.04	13	7346	3867	46674836
Polyneuropathy	27.26	24.04	19	7340	11625	46667078
Multiple organ dysfunction syndrome	25.68	24.04	36	7323	51674	46627029
Hepatitis E	25.68	24.04	9	7350	1230	46677473
Candida sepsis	24.99	24.04	9	7350	1330	46677373
Hyperuricaemia	24.95	24.04	13	7346	4704	46673999
Posterior reversible encephalopathy syndrome	24.93	24.04	20	7339	15121	46663582

FDA Adverse Event Reporting System (Male)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Febrile neutropenia	416.05	21.10	291	7768	106402	29838017
Encephalopathy	264.88	21.10	142	7917	32063	29912356
Cystitis haemorrhagic	138.06	21.10	51	8008	4736	29939683
Venoocclusive liver disease	115.38	21.10	49	8010	6564	29937855
Pyrexia	91.47	21.10	226	7833	294263	29650156
Pancytopenia	84.49	21.10	109	7950	84943	29859476
Neutropenia	84.07	21.10	135	7924	128405	29816014
Febrile bone marrow aplasia	81.60	21.10	41	8018	8056	29936363
Mucosal inflammation	73.81	21.10	63	7996	30431	29913988
Cytokine release syndrome	65.62	21.10	38	8021	9895	29934524
Haematotoxicity	61.45	21.10	31	8028	6139	29938280
Aplasia	60.88	21.10	27	8032	4010	29940409
Leukopenia	60.49	21.10	75	7984	56084	29888335
Thrombocytopenia	60.10	21.10	121	7938	136923	29807496
Fanconi syndrome	58.96	21.10	21	8038	1754	29942665
Venoocclusive disease	58.15	21.10	23	8036	2567	29941852
Neutrophil count decreased	46.18	21.10	57	8002	42397	29902022
Acute graft versus host disease	45.68	21.10	25	8034	5839	29938580
Foetal growth restriction	41.62	21.10	20	8039	3565	29940854
Neurotoxicity	39.80	21.10	31	8028	13151	29931268
Angiodysplasia	38.17	21.10	11	8048	463	29943956
Polyneuropathy	33.96	21.10	27	8032	11796	29932623
Fusarium infection	33.12	21.10	12	8047	1052	29943367
Fall	32.65	21.10	5	8054	181867	29762552
Stomatitis	31.16	21.10	44	8015	37235	29907184
Bone marrow failure	30.79	21.10	39	8020	29746	29914673
Myelosuppression	30.69	21.10	21	8038	7301	29937118
Drug ineffective	30.66	21.10	28	8031	340359	29604060
Chronic graft versus host disease	30.54	21.10	17	8042	4102	29940317
Acute graft versus host disease in skin	29.08	21.10	17	8042	4499	29939920
Septic shock	27.59	21.10	56	8003	63551	29880868
Death	27.03	21.10	34	8025	357249	29587170
Staphylococcal bacteraemia	25.08	21.10	18	8041	6750	29937669
Non-Hodgkin's lymphoma unspecified histology aggressive	24.71	21.10	5	8054	44	29944375
Drug therapeutic incompatibility	24.59	21.10	6	8053	131	29944288
Cytomegalovirus hepatitis	24.07	21.10	7	8052	304	29944115
Off label use	24.02	21.10	131	7928	249159	29695260
Anaemia	24.01	21.10	115	7944	207877	29736542
Myocardial infarction	23.59	21.10	3	8056	125622	29818797
Osmotic demyelination syndrome	22.34	21.10	8	8051	678	29943741
Pulpitis dental	22.23	21.10	7	8052	399	29944020
Low birth weight baby	22.15	21.10	16	8043	6060	29938359
Chloroma	21.59	21.10	7	8052	439	29943980
Agranulocytosis	21.52	21.10	28	8031	21914	29922505
Pulmonary toxicity	21.45	21.10	14	8045	4502	29939917
Toxic encephalopathy	21.18	21.10	14	8045	4595	29939824

Pharmacologic Action:

Source	Code	Description
ATC	R05CB05	RESPIRATORY SYSTEM COUGH AND COLD PREPARATIONS EXPECTORANTS, EXCL. COMBINATIONS WITH COUGH SUPPRESSANTS Mucolytics
ATC	V03AF01	VARIOUS ALL OTHER THERAPEUTIC PRODUCTS ALL OTHER THERAPEUTIC PRODUCTS Detoxifying agents for antineoplastic treatment
MeSH PA	D020011	Protective Agents
CHEBI has role	CHEBI:23354	coenzymes

Drug Use (View source of the data)

Disease	Relation	SNOMED_ID	DOID
Testicular Germ Cell Tumor	indication
Prevention of Chemotherapy-Induced Hemorrhagic Cystitis	indication
Ewing's sarcoma	off-label use	76909002	DOID:3369
Burkitt's lymphoma	off-label use	118617000
Non-small cell lung cancer	off-label use	254637007	DOID:3908
Malignant tumor of head and/or neck	off-label use	255056009
Osteosarcoma of bone	off-label use	307576001	DOID:3376
Soft or Connective Tissue Sarcoma	off-label use
Renal tubular acidosis	contraindication	1776003	DOID:14219
Hyperbilirubinemia	contraindication	14783006	DOID:2741
Dehydration	contraindication	34095006
Fanconi syndrome	contraindication	40488004	DOID:1062
Hypokalemia	contraindication	43339004
Leukopenia	contraindication	84828003	DOID:615
Kidney disease	contraindication	90708001	DOID:557
Kidney excision	contraindication	108022006
Liver function tests abnormal	contraindication	166603001
Disease of liver	contraindication	235856003	DOID:409
Impaired wound healing	contraindication	271618001
Anemia	contraindication	271737000	DOID:2355
Pregnancy, function	contraindication	289908002
Thrombocytopenic disorder	contraindication	302215000	DOID:1588
Bone marrow depression	contraindication	307762000
Coma	contraindication	371632003
Impaired cognition	contraindication	386806002
Breastfeeding (mother)	contraindication	413712001
Cancer Chemotherapy Induced Hemorrhagic Cystitis	contraindication
Polyneuropathies	contraindication
Severe Bone Marrow Depression	contraindication
Bone Metastases	contraindication
CNS Toxicity	contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	0.61	acidic
pKa2	9.77	acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

None

External reference:

ID	Source
4019477	VUID
N0000147597	NUI
D01459	KEGG_DRUG
19767-45-4	SECONDARY_CAS_RN
4019477	VANDF
C0000294	UMLSCUI
CHEBI:17905	CHEBI
COM	PDB_CHEM_ID
CHEMBL975	ChEMBL_ID
CHEMBL1098319	ChEMBL_ID
D015080	MESH_DESCRIPTOR_UI
DB09110	DRUGBANK_ID
2813	INN_ID
NR7O1405Q9	UNII
23662354	PUBCHEM_CID
1546354	RXNORM
41498	MMSL
5057	MMSL
d01411	MMSL
002678	NDDF
108821000	SNOMEDCT_US
386922000	SNOMEDCT_US

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
MESNEX	HUMAN PRESCRIPTION DRUG LABEL	1	0338-1305	INJECTION, SOLUTION	100 mg	INTRAVENOUS	NDA	27 sections
MESNULL	HUMAN PRESCRIPTION DRUG LABEL	1	10019-951	INJECTION, SOLUTION	100 mg	INTRAVENOUS	NDA	26 sections
MESNULL	HUMAN PRESCRIPTION DRUG LABEL	1	10019-953	INJECTION, SOLUTION	100 mg	INTRAVENOUS	NDA	26 sections
Mesna	HUMAN PRESCRIPTION DRUG LABEL	1	25021-201	INJECTION, SOLUTION	100 mg	INTRAVENOUS	ANDA	26 sections
Mesna	HUMAN PRESCRIPTION DRUG LABEL	1	25021-201	INJECTION, SOLUTION	100 mg	INTRAVENOUS	ANDA	26 sections
Mesna	Human Prescription Drug Label	1	63323-733	INJECTION, SOLUTION	100 mg	INTRAVENOUS	ANDA	27 sections
MESNEX	HUMAN PRESCRIPTION DRUG LABEL	1	67108-3565	TABLET, FILM COATED	400 mg	ORAL	NDA	26 sections
Mesna	Human Prescription Drug Label	1	68083-161	SOLUTION	100 mg	INTRAVENOUS	ANDA	26 sections
Mesna	HUMAN PRESCRIPTION DRUG LABEL	1	70860-209	INJECTION, SOLUTION	100 mg	INTRAVENOUS	ANDA	27 sections