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Details

Stereochemistry ACHIRAL
Molecular Formula C13H8Cl2N2O4.C2H7NO
Molecular Weight 388.203
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NICLOSAMIDE-OLAMINE

SMILES

NCCO.OC1=CC=C(Cl)C=C1C(=O)NC2=C(Cl)C=C(C=C2)[N+]([O-])=O

InChI

InChIKey=XYCDHXSQODHSLG-UHFFFAOYSA-N
InChI=1S/C13H8Cl2N2O4.C2H7NO/c14-7-1-4-12(18)9(5-7)13(19)16-11-3-2-8(17(20)21)6-10(11)15;3-1-2-4/h1-6,18H,(H,16,19);4H,1-3H2

HIDE SMILES / InChI

Molecular Formula C13H8Cl2N2O4
Molecular Weight 327.12
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C2H7NO
Molecular Weight 61.0831
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Niclosamide is an antihelminth used against tapeworm infections. It may act by the uncoupling of the electron transport chain to ATP synthase. The disturbance of this crucial metabolic pathway prevents creation of adenosine tri-phosphate (ATP), an essential molecule that supplies energy for metabolism. Niclosamide works by killing tapeworms on contact. Adult worms (but not ova) are rapidly killed, presumably due to uncoupling of oxidative phosphorylation or stimulation of ATPase activity. The killed worms are then passed in the stool or sometimes destroyed in the intestine. Niclosamide may work as a molluscicide by binding to and damaging DNA. Niclosamide is used for the treatment of tapeworm and intestinal fluke infections: Taenia saginata (Beef Tapeworm), Taenia solium (Pork Tapeworm), Diphyllobothrium latum (Fish Tapeworm), Fasciolopsis buski (large intestinal fluke). Niclosamide is also used as a molluscicide in the control of schistosomiasis. Niclosamide was marketed under the trade name Niclocide, now discontinued.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
2.7 µM [Ki]
45.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
NICLOCIDE
Curative
NICLOCIDE
Curative
NICLOCIDE

Cmax

ValueDoseCo-administeredAnalytePopulation
0.665 μg/mL
2 g single, oral
NICLOSAMIDE plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Adults—2 grams as a single dose. Treatment may be repeated in seven days if needed.
Route of Administration: Oral
In Vitro Use Guide
Niclosamide (0.2 ug/ml) was effective against Diplozoon paradoxum after an exposure of 90 min and 45 min in vitro.
Substance Class Chemical
Record UNII
QT8YUD1Z0W
Record Status Validated (UNII)
Record Version