SULFALENE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H12N4O3S
Molecular Weight	280.303
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=NC=CN=C1NS(=O)(=O)C2=CC=C(N)C=C2

InChI

InChIKey=KXRZBTAEDBELFD-UHFFFAOYSA-N

InChI=1S/C11H12N4O3S/c1-18-11-10(13-6-7-14-11)15-19(16,17)9-4-2-8(12)3-5-9/h2-7H,12H2,1H3,(H,13,15)

HIDE SMILES / InChI

Molecular Formula	C11H12N4O3S
Molecular Weight	280.303
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.drugbank.ca/drugs/DB00664
Curator's Comment: description was created based on several sources, including https://www.drugs.com/international/sulfalene.html | https://www.ncbi.nlm.nih.gov/pubmed/137981 | https://www.ncbi.nlm.nih.gov/pubmed/4888027 | https://www.ncbi.nlm.nih.gov/pubmed/5864358

Sulfalene (INN, USAN) or Sulfametopyrazine (BAN) is a long-acting sulfonamide antibiotic used for the treatment of chronic bronchitis, urinary tract infections, and malaria. Sulfametopyrazine, by virtue of a long half-life, achieves peak blood levels of 120 mkg/ml or more which fall to around 30-50 mkg/ml one week after a single oral dose of 2 g. Long-term administration of this drug in the treatment of leprosy for up to 3 years has been accomplished without serious unwanted effects

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial dihydropteroate synthase 44 Target ID: CHEMBL2364668 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25775967	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Malaria 96 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4888027	Curative	Approved 8583	Kelfizina Approved Use Unknown
Bronchitis 51 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4563330	Primary	Approved 8583	Sulfametopyrazine Approved Use Unknown
Leprosy 5 Sources: https://www.cabdirect.org/cabdirect/abstract/19682902237	Primary	Not Provided 511	Kelfizina Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
65 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7410285/	200 mg 1 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: TRIMETHOPRIM	TRIMETHOPRIM	SULFALENE plasma	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
59.4 h EXPERIMENT https://link.springer.com/content/pdf/10.1007/BF00773103.pdf	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:		SULFALENE unknown	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: FASTED
70 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7410285/	200 mg 1 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: TRIMETHOPRIM	TRIMETHOPRIM	SULFALENE plasma	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
200 mg 1 times / day multiple, oral Studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6340974/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6340974/	Disc. AE: Exanthema... AEs leading to discontinuation/dose reduction: Exanthema (2.9%) Sources: https://pubmed.ncbi.nlm.nih.gov/6340974/
250 mg 1 times / day multiple, oral Studied dose Dose: 250 mg, 1 times / day Route: oral Route: multiple Dose: 250 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20705516/	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/20705516/	Sources: https://pubmed.ncbi.nlm.nih.gov/20705516/

AEs

AE	Significance	Dose	Population
Exanthema	2.9% Disc. AE	200 mg 1 times / day multiple, oral Studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6340974/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6340974/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1087 inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2057 CYP19A1 429 CYP1A2 2153	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/9047#section=Biological-Test-Results Page: 149.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/9047#section=Biological-Test-Results Page: 208.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/9047#section=Biological-Test-Results Page: 207.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/9047#section=Biological-Test-Results Page: 196.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/9047#section=Biological-Test-Results Page: 201.0	no
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/9047#section=Biological-Test-Results Page: 194.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/9047#section=Biological-Test-Results Page: 197.0	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/9047#section=Biological-Test-Results Page: 193 \| 196	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/9047#section=Biological-Test-Results Page: 208.0

PubMed

Title	Date	PubMed
In vivo effect of piperine on serum and tissue glycoprotein levels in benzo(a)pyrene induced lung carcinogenesis in Swiss albino mice.	2006	15975841
Rapid identification of potentially probiotic Bifidobacterium species by multiplex PCR using species-specific primers based on the region extending from 16S rRNA through 23S rRNA.	2005-09-01	16039804
Culture-dependent and culture-independent qualitative analysis of probiotic products claimed to contain bifidobacteria.	2005-07-15	15992621
Piperine from the fruits of Piper longum with inhibitory effect on monoamine oxidase and antidepressant-like activity.	2005-07	15997146
Phytase activity as a novel metabolic feature in Bifidobacterium.	2005-06-15	15935567
Optimization of a Bifidobacterium longum production process.	2005-05-25	15862361
The TyrA family of aromatic-pathway dehydrogenases in phylogenetic context.	2005-05-12	15888209
A proteomic view of Bifidobacterium infantis generated by multi-dimensional chromatography coupled with tandem mass spectrometry.	2005-05	15619299
The effects of extracts from anti-diarrheic Thai medicinal plants on the in vitro growth of the intestinal protozoa parasite: Blastocystis hominis.	2005-04-08	15763365
Identification to the species level of Lactobacillus isolated in probiotic prospecting studies of human, animal or food origin by 16S-23S rRNA restriction profiling.	2005-03-23	15788104
A novel firmicute protein family related to the actinobacterial resuscitation-promoting factors by non-orthologous domain displacement.	2005-03-17	15774001
Chemopreventive effect of piperine on mitochondrial TCA cycle and phase-I and glutathione-metabolizing enzymes in benzo(a)pyrene induced lung carcinogenesis in Swiss albino mice.	2005-03	15881660
Structural and functional analysis of pTB6 from Bifidobacterium longum.	2005-02	15725673
Bifidobacterium longum as an oral delivery system of endostatin for gene therapy on solid liver cancer.	2005-02	15565182
Oral supplementation of piperine leads to altered phase II enzymes and reduced DNA damage and DNA-protein cross links in Benzo(a)pyrene induced experimental lung carcinogenesis.	2005-01	15724447
Growth of Bifidobacterium longum BB536 in medida (fermented cereal porridge) and their survival during refrigerated storage.	2005	16033508
The genomics of probiotic intestinal microorganisms.	2005	15998456
Lactic acid production from cheese whey by immobilized bacteria.	2005	15920260
Herb-drug interactions: a literature review.	2005	15916450
Effect of an indigenous herbal compound preparation 'Trikatu' on the lipid profiles of atherogenic diet and standard diet fed Rattus norvegicus.	2004-12	15742354
Piperlonguminine from Piper longum with inhibitory effects on alpha-melanocyte-stimulating hormone-induced melanogenesis in melanoma B16 cells.	2004-12	15643542
Comparative detection of bacterial adhesion to Caco-2 cells with ELISA, radioactivity and plate count methods.	2004-11	15369857
Nutrition and cancer: a review of the evidence for an anti-cancer diet.	2004-10-20	15496224
Is autoinducer-2 a universal signal for interspecies communication: a comparative genomic and phylogenetic analysis of the synthesis and signal transduction pathways.	2004-09-29	15456522
Development of multi-color FISH method for analysis of seven Bifidobacterium species in human feces.	2004-09	15279945
Selection of acid tolerant bifidobacteria and evidence for a low-pH-inducible acid tolerance response in Bifidobacterium longum.	2004-08	15354581
Guineensine, an Acyl-CoA: cholesterol acyltransferase inhibitor, from the fruits of Piper longum.	2004-07	15254860
Bifidobacterial species differentially affect expression of cell surface markers and cytokines of dendritic cells harvested from cord blood.	2004-07	15242942
Clinical experience with probiotics in the elderly on total enteral nutrition.	2004-07	15220673
Preparative isolation and purification of amides from the fruits of Piper longum L. by upright counter-current chromatography and reversed-phase liquid chromatography.	2004-06-25	15230526
[Search of promising strains of bifidobacteria and lactobacillus for the development of new biopreparations].	2004-06-11	15188563
Viability of lactic acid bacteria and bifidobacteria in fermented soymilk after drying, subsequent rehydration and storage.	2004-06-01	15135959
Growth-promoting effects of lactoferrin on L. acidophilus and Bifidobacterium spp.	2004-06	15222478
Isolation and synthesis of isodihydropiperlonguminine.	2004-06	15143835
Effects of Piper longum fruit, Piper sarmentosum root and Quercus infectoria nut gall on caecal amoebiasis in mice.	2004-04	15120461
Pharmacokinetic and pharmacodynamic studies on interaction of "Trikatu" with diclofenac sodium.	2004-04	15120451
The PAV trial: does lactobacillus prevent post-antibiotic vulvovaginal candidiasis? Protocol of a randomised controlled trial [ISRCTN24141277].	2004-03-28	15046642
Immunomodulatory and antitumor effects in vivo by the cytoplasmic fraction of Lactobacillus casei and Bifidobacterium longum.	2004-03	15028884
In vitro digestion of sinigrin and glucotropaeolin by single strains of Bifidobacterium and identification of the digestive products.	2004-03	14871576
Spectrophotometric method for estimation of alkaloids precipitable with Dragendorff's reagent in plant materials.	2004-02-26	14979692
Immunomodulatory and antitumor activity of Piper longum Linn. and piperine.	2004-02	15013199
Anti-inflammatory activities of Aller-7, a novel polyherbal formulation for allergic rhinitis.	2004	15573692
Antioxidant properties of Aller-7, a novel polyherbal formulation for allergic rhinitis.	2004	15366786
Increased stress tolerance of Bifidobacterium longum and Lactococcus lactis produced during continuous mixed-strain immobilized-cell fermentation.	2004	15281933
Genetic heterogeneity and functional properties of intestinal bifidobacteria.	2004	15281925
Enumeration, isolation, and identification of bifidobacteria from infant feces.	2004	15227800
Effect of Bifidobacterium longum ingestion on experimental salmonellosis in mice.	2004	15186439
Comparative genomics of gene-family size in closely related bacteria.	2004	15059260
Analgesic activity of Piper longum Linn. root.	2003-06	15266916
Enzymatic and non-enzymatic antioxidants in selected Piper species.	2003-02	15255605

Patents

Sample Use Guides

In Vivo Use Guide

Adults with acute diseases on day 1 - 1 g, then 200 mg / day. The duration of the course is 7-10 days. With chronic, long-term infections (with chronic lung diseases, rheumatism, kidney and urinary tract diseases) - 2 g in 1 dose once a week.

Route of Administration: Oral

In Vitro Use Guide

The bacteria Streptococcus faecium durans (Streptococcus faecalis ATCC 8043), Lactobacillus casei ATCC 7469, Pediococcus cereuisiae ATCC 8081, and Escherichia coli ATCC 10536 were used for activity evaluation. Amounts of 8 ml of the appropriate basal medium were placed in tubes and sterilized by autoclaving at 121 C for 10 min. Folic acid or calcium leucovorin diluted in 25% sterile glucose solution was added in 1-ml quantities. The final concentrations of folic acid were 0.002 ,ug/ml for S. faecium and 0.001 ,ug/ml for L. casei; the final concentration of calcium leucovorin was 0.001 ,ug/ml for P. cerevisiae. Stock solutions of PM in 0.04 N HCl and of CGT, TMP, and MTX in distilled water were sterilized by membrane filtration. SULFALENE dilutions in 1 ml of distilled water were added to give a final volume of 10 ml. Growth of the test organisms was read as turbidity in the Klett-Summerson photoelectric colorimeter. The results are expressed as the micromolar concentration required to produce 50% growth inhibition (ICs,) of the strain under the conditions used. Where sufficient drug was available, concentrations up to 1000 mkg/ml were tested; when this was not possible the highest concentration used was 100 mkg/ml.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:35:40 GMT 2025` Edited by `admin` on `Mon Mar 31 17:35:40 GMT 2025`
Record UNII	T6BL4ZC15G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SULFALENE

Official Name

English

SULFAMETHOPYRAZINE

Preferred Name

English

BENZENESULFONAMIDE, 4-AMINO-N-(3-METHOXYPYRAZINYL)-

Systematic Name

English

AS-18908

Code

English

N(SUP 1)-(3-METHOXYPYRAZINYL)SULFANILAMIDE

Systematic Name

English

SULFAMETOPYRAZINE [MART.]

Common Name

English

SULFALENE [MI]

Common Name

English

NSC-110433

Code

English

sulfalene [INN]

Common Name

English

Sulfalene [WHO-DD]

Common Name

English

SULFAMETOPYRAZINE

Common Name

English

SULFAMETHOXYPYRAZINE

Common Name

English

SULFALENE [USAN]

Common Name

English

SULFAMETHOPYRAZINE [JAN]

Common Name

English

Classification Tree Code System Code

WHO-ATC

J01ED02