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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H45N5O14
Molecular Weight 615.6294
Optical Activity UNSPECIFIED
Defined Stereocenters 19 / 19
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PAROMOMYCIN

SMILES

C1[C@]([H])([C@@]([H])([C@]([H])([C@@]([H])([C@@]1([H])N)O[C@]2([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(CO)O2)O)O)N)O[C@@]3([H])[C@@]([H])([C@@]([H])([C@@]([H])(CO)O3)O[C@]4([H])[C@@]([H])([C@]([H])([C@@]([H])([C@]([H])(CN)O4)O)O)N)O)O)N

InChI

InChIKey=UOZODPSAJZTQNH-LSWIJEOBSA-N
InChI=1S/C23H45N5O14/c24-2-7-13(32)15(34)10(27)21(37-7)41-19-9(4-30)39-23(17(19)36)42-20-12(31)5(25)1-6(26)18(20)40-22-11(28)16(35)14(33)8(3-29)38-22/h5-23,29-36H,1-4,24-28H2/t5-,6+,7+,8-,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+/m1/s1

HIDE SMILES / InChI
Molecular Formula C23H45N5O14
Molecular Weight 615.6294
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 19 / 19
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: Description was created based on several sources, including http://www.drugs.com/cdi/paromomycin.html http://www.rxmed.com/b.main/b2.pharmaceutical/b2.1.monographs/CPS-%20Monographs/CPS-%20%28General%20Monographs-%20H%29/HUMATIN.html

Paromomycin is a broad spectrum aminoglycoside antibiotic produced by by Streptomyces rimosus var. paromomycinus and used to treat intestinal infections such as cryptosporidiosis and amoebiasis, and other diseases such as leishmaniasis. Paromomycin is also used for the management of hepatic coma as adjunctive therapy. Paromomycin inhibits protein synthesis by binding to bacterial or protozoal 16S ribosomal RNA which causes defective polypeptide chains to be produced. Continuous production of defective proteins eventually leads to bacterial death. Gastrointestinal side effects include nausea, vomiting, diarrhea, and abdominal discomfort.

Originator

Parke Davis
57
Curator's Comment:: Paromomycin was discovered by Parke Davis now Pfizer and introduced as Humatin in 1960.

Approval Year

1960
96
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
7728
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8043
PAROMOMYCIN SULFATE

Approved Use

Paromomycin sulfate is indicated for intestinal amebiasis—acute and chronic (NOTE—It is not effective in extraintestinal amebiasis); management of hepatic coma—as adjunctive therapy.

Launch Date

1.19759045E12
Secondary
Approved
8043
PAROMOMYCIN SULFATE

Approved Use

Paromomycin sulfate is indicated for intestinal amebiasis—acute and chronic (NOTE—It is not effective in extraintestinal amebiasis); management of hepatic coma—as adjunctive therapy.

Launch Date

1.19759045E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
331 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/23877689
150 mg single, topical
dose: 150 mg
route of administration: Topical
experiment type: SINGLE
co-administered:
PAROMOMYCIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1000 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/23877689
150 mg 1 times / day multiple, topical
dose: 150 mg
route of administration: Topical
experiment type: MULTIPLE
co-administered:
PAROMOMYCIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
2180 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/23877689
150 mg single, topical
dose: 150 mg
route of administration: Topical
experiment type: SINGLE
co-administered:
PAROMOMYCIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
8575 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/23877689
150 mg 1 times / day multiple, topical
dose: 150 mg
route of administration: Topical
experiment type: MULTIPLE
co-administered:
PAROMOMYCIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5.04 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/23877689
150 mg single, topical
dose: 150 mg
route of administration: Topical
experiment type: SINGLE
co-administered:
PAROMOMYCIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
5.96 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/23877689
150 mg 1 times / day multiple, topical
dose: 150 mg
route of administration: Topical
experiment type: MULTIPLE
co-administered:
PAROMOMYCIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
100%
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/28756612
PAROMOMYCIN unknown
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
P-gp
1400

CYP
236
OCT1
19
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
OCT1
495
 likely
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP
236
 yes
P-gp
1400
 yes
yes (co-administration study)
Comment: verapamil increased paromomycin exposure 1.5x
Page: abstract
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:7934
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7934
ChemicalBook
CB6911922
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6911922
MolPort
MolPort-002-510-747
https://www.molport.com/shop/molecule-link/MolPort-002-510-747
ZINC
ZINC000060183170
http://zinc15.docking.org/substances/ZINC000060183170
eMolecules
4786830
https://www.emolecules.com/cgi-bin/more?vid=4786830
PubMed

PubMed

TitleDatePubMed
[Considerations and results of the use of paramomycin in the prevention of infectious complications in colorectal surgery].
2002 Apr
Fluconazole for the treatment of cutaneous leishmaniasis.
2002 Aug 1
Stereospecificity of aminoglycoside-ribosomal interactions.
2002 Aug 20
Evaluation of in vitro and in vivo activity of benzindazole-4,9-quinones against Cryptosporidium parvum.
2002 Dec
"Chemotherapeutic approaches to protozoa: Giardia, Trichomonas and Entamoeba-current level of knowledge and outlook".
2002 Jun
Footprinting and circular dichroism studies on paromomycin binding to the packaging region of human immunodeficiency virus type-1.
2002 Nov
Detecting ligand binding to a small RNA target via saturation transfer difference NMR experiments in D(2)O and H(2)O.
2002 Nov 13
Controlling the onset of natural cryptosporidiosis in calves with paromomycin sulphate.
2002 Nov 16
Selection of tRNA by the ribosome requires a transition from an open to a closed form.
2002 Nov 27
Treatment of asymptomatic intestinal Entamoeba histolytica infection.
2002 Oct 24
Identification of a role for actin in translational fidelity in yeast.
2002 Sep
The protein synthesis inhibitors, oxazolidinones and chloramphenicol, cause extensive translational inaccuracy in vivo.
2002 Sep 13
Various effects of paromomycin on tmRNA-mediated trans-translation.
2003
Treatment of cutaneous leishmaniasis with aminosidine (paromomycin) ointment: double-blind, randomized trial in the Islamic Republic of Iran.
2003
Comparative study of the prophylactic and therapeutic effects of paromomycin, recombinant IL-12 alone or in combination against Cryptosporidium parvum infection in immunosuppressed mice.
2003 Apr
Eradication of Cryptosporidium in four children with acute lymphoblastic leukemia.
2003 Apr
Evaluation of rye (Secale cereale L.) inbred lines and their crosses for tissue culture response and stable genetic transformation of homozygous rye inbred line L22 by biolistic gene transfer.
2003 Aug
Rubisco activase is required for optimal photosynthesis in the green alga Chlamydomonas reinhardtii in a low-CO(2) atmosphere.
2003 Dec
Crystal structure of geneticin bound to a bacterial 16S ribosomal RNA A site oligonucleotide.
2003 Feb 28
Treatment of cutaneous leishmaniasis with either topical paromomycin or intralesional meglumine antimoniate.
2003 Jan
Comparison of X-ray crystal structure of the 30S subunit-antibiotic complex with NMR structure of decoding site oligonucleotide-paromomycin complex.
2003 Jan
HIV-1 RNA dimerization initiation site is structurally similar to the ribosomal A site and binds aminoglycoside antibiotics.
2003 Jan 24
A dispensable yeast ribosomal protein optimizes peptidyltransferase activity and affects translocation.
2003 Jan 31
Selective enumeration of Lactobacillus delbrueckii ssp. bulgaricus, Streptococcus thermophilus, Lactobacillus acidophilus, bifidobacteria, Lactobacillus casei, Lactobacillus rhamnosus, and propionibacteria.
2003 Jul
Production of Hevea brasiliensis transgenic embryogenic callus lines by Agrobacterium tumefaciens: roles of calcium.
2003 Jul
Various effects of paromomycin on tmRNA-directed trans-translation.
2003 Jul 25
Design and synthesis of paromomycin-related heterocycle-substituted aminoglycoside mimetics based on a mass spectrometry RNA-binding assay.
2003 Jul 28
Aminoglycosides suppress tRNA processing in human epidermal keratinocytes in vitro.
2003 Jul-Aug
Treatment of cutaneous leishmaniasis by photodynamic therapy.
2003 Jun
[Cutaneous leishmaniasis].
2003 Jun
Effect of neomycin B on rotavirus plus- and minus-strand RNA synthesis.
2003 Jun
Long-lasting anticryptosporidial activity of nitazoxanide in an immunosuppressed rat model.
2003 Mar
The complex of a designer antibiotic with a model aminoacyl site of the 30S ribosomal subunit revealed by X-ray crystallography.
2003 Mar 26
Coupling of drug protonation to the specific binding of aminoglycosides to the A site of 16 S rRNA: elucidation of the number of drug amino groups involved and their identities.
2003 Mar 7
Insights into the decoding mechanism from recent ribosome structures.
2003 May
Aminoglycoside complexation with a DNA.RNA hybrid duplex: the thermodynamics of recognition and inhibition of RNA processing enzymes.
2003 May 28
Structure-activity relationship of neomycin, paromomycin, and neamine-arginine conjugates, targeting HIV-1 gp120-CXCR4 binding step.
2003 Nov
Vibrational Markovian modelling of footprints after the interaction of antibiotics with the packaging region of HIV type 1.
2003 Nov
Efficacy of antigiardial drugs.
2003 Nov
Markovian negentropies in bioinformatics. 1. A picture of footprints after the interaction of the HIV-1 Psi-RNA packaging region with drugs.
2003 Nov 1
Sfp1 plays a key role in yeast ribosome biogenesis.
2003 Oct
Entamoeba histolytica: an update.
2003 Oct
Current treatment approaches to leishmaniasis.
2003 Oct
The molecular basis for A-site mutations conferring aminoglycoside resistance: relationship between ribosomal susceptibility and X-ray crystal structures.
2003 Oct 6
[Liver abscess: a practical approach].
2003 Oct 8
Neomycin and paromomycin inhibit 30S ribosomal subunit assembly in Staphylococcus aureus.
2003 Sep
Multitarget affinity/specificity screening of natural products: finding and characterizing high-affinity ligands from complex mixtures by using high-performance mass spectrometry.
2003 Sep
Thermodynamics of aminoglycoside-rRNA recognition.
2003 Sep
Effect of antiretroviral protease inhibitors alone, and in combination with paromomycin, on the excystation, invasion and in vitro development of Cryptosporidium parvum.
2003 Sep
Genetic transformation of Indian bread (T. aestivum) and pasta (T. durum) wheat by particle bombardment of mature embryo-derived calli.
2003 Sep 3
Patents

Patents

JP2010531845A
7

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: Additional resource: http://www.rxlist.com/paromomycin-sulfate-drug.htm
Intestinal amebiasis: 25 to 35 mg/kg body weight daily, administered in three doses with meals, for five to ten days. Management of hepatic coma: 4 g daily in divided doses, given at regular intervals for five to six days.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment:: Paromomycin inhibited the growth of Cryptosporidium parvum in Madin-Darby canine kidney (MDCK) cells in a dose-dependent manner. The EC50s of paromomycin against C. parvum growth in MDCK cells was 1184 mg/L. Paromomycin at 25, 50 and 100 μg/ml, inhibited the growth of Leishmania major amastigotes by 34.5%, 61.2%, 74.9% and 85.4%, 89.9%, 95.7% on the 2nd and the 4th day of treatment in culture, respectively (http://www.sciencedirect.com/science/article/pii/S0014489406003262).
1184 mg/L
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:35:29 UTC 2021
Edited
by admin
on Fri Jun 25 20:35:29 UTC 2021
Record UNII
61JJC8N5ZK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PAROMOMYCIN
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
R-400
Code English
NEOMYCIN SULFATE IMPURITY E [EP]
Common Name English
PAROMOMYCIN [WHO-DD]
Common Name English
CRESTOMYCIN
Common Name English
CATENULIN
Common Name English
QUINTOMYCIN C
Common Name English
ANTIBIOTIC SF-767B
Code English
PAUCIMYCIN
Common Name English
PAROMOMYCIN [VANDF]
Common Name English
DIAMINO-2,6-DIDEOXY-.BETA.-L-IDOPYRANOSYL-(1->3)-O-.BETA.-D-RIBOFURANOSYL-(1->5)-O-(2-AMINO-2-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4))-2-DEOXYSTREPTAMINE
Common Name English
GABROMYCIN
Common Name English
O-2-AMINO-2-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-O-(O-2,6-DIAMINO-2,6-DIDEOXY-.BETA.-L-IDOPYRANOSYL-(1->3)-.BETA.-D-RIBOFURANOSYL-(1->5))-2-DEOXY-D-STREPTAMINE
Common Name English
NEOMYCIN E
Common Name English
HYDROXYMYCIN
Common Name English
PAROMOMYCIN [INN]
Common Name English
MONOMYCIN A
Common Name English
ANTIBIOTIC 503-3
Code English
AMINOSIDIN
Common Name English
PAROMOMYCIN [MI]
Common Name English
D-STREPTAMINE, O-2-AMINO-2-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-O-(O-2,6-DIAMINO-2,6-DIDEOXY-.BETA.-L-IDOPYRANOSYL-(1->3)-.BETA.-D-RIBOFURANOSYL-(1->5))-2-DEOXY-
Common Name English
PAROMOMYCIN I
Common Name English
ESTOMYCIN
Common Name English
O-2,6-DIAMINO-2,6-DIDEOXY-.BETA.-L-IDOPYRANOSYL-(1->3)-O-.BETA.-D-RIBOFURANOSYL-(1->5)-O-(2-AMINO-2-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4))-2-DEOXYSTREPTAMINE
Common Name English
Classification Tree Code System Code
WHO-VATC QA07AA06
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
WHO-ATC A07AA06
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 6.5.2
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
NCI_THESAURUS C2363
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
FDA ORPHAN DRUG 464314
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
NDF-RT N0000175485
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
Code System Code Type Description
DRUG BANK
DB01421
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
PRIMARY
EPA CompTox
7542-37-2
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
PRIMARY
INN
939
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
PRIMARY
ECHA (EC/EINECS)
231-423-0
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
PRIMARY
EVMPD
SUB09630MIG
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
PRIMARY
FDA UNII
61JJC8N5ZK
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
PRIMARY
LACTMED
Paromomycin
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
PRIMARY
PUBCHEM
165580
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
PRIMARY
NCI_THESAURUS
C61878
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PRIMARY
ChEMBL
CHEMBL370143
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PRIMARY
CAS
7542-37-2
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
PRIMARY
DRUG CENTRAL
2067
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PRIMARY
MESH
D010303
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
PRIMARY
MERCK INDEX
M8416
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
PRIMARY Merck Index
RXCUI
7934
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
PRIMARY RxNorm
WIKIPEDIA
PAROMOMYCIN
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
PRIMARY
Related Record Type Details
Structure of PAROMOMYCIN SULFATE
SALT/SOLVATE -> PARENT
Related Record Type Details
NEOMYCIN SULFATE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of PAROMOMYCIN
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