Details of the Drug

General Information of Drug (ID: DMWA2DZ)

Drug Name

Berotralstat

Synonyms

UNII-XZA0KB1BDQ; XZA0KB1BDQ; 1809010-50-1; BCX7353; BCX-7353; Berotralstat (USAN); Berotralstat [USAN]; 1-[3-(aminomethyl)phenyl]-N-(5-{(R)-(3-; cyanophenyl)[(cyclopropylmethyl)amino]methyl}-2-; fluorophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-; Orladeyo; Berotralstat [INN]; Berotralstat [USAN:INN]; SCHEMBL21974728; GTPL11347; WHO 10907; D11673; 1-(3-(Aminomethyl)phenyl)-N-(5-((R)-(3-cyanophenyl)((cyclopropylmethyl)amino)methyl)-2-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide; 1H-pyrazole-5-carboxamide, 1-(3-(aminomethyl)phenyl)-N-(5-((R)-(3-cyanophenyl)((cyclopropylmethyl); 1H-Pyrazole-5-carboxamide, 1-(3-(aminomethyl)phenyl)-N-(5-((R)-(3-cyanophenyl)((cyclopropylmethyl)amino)methyl)-2-fluorophenyl)-3-(trifluoromethyl)-; 2-[3-(aminomethyl)phenyl]-N-[5-[(R)-(3-cyanophenyl)-(cyclopropylmethylamino)methyl]-2-fluorophenyl]-5-(trifluoromethyl)pyrazole-3-carboxamide

Indication

Disease Entry	ICD 11	Status	REF
Hereditary angioedema	4A00.14	Approved	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

562.6

Logarithm of the Partition Coefficient (xlogp)

4.5

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption AUC: The area under the plot of plasma concentration (AUC) of drug is 2770 mcgh/L [2]
Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 158 mcg/L [2]
Absorption Tmax: The time to maximum plasma concentration (Tmax) is 2 h [2]
Elimination: Following a single oral dose administration of 300 mg radiolabeled berotralstat, approximately 9% of the drug was excreted in the urine, where 1.8 to 4.7% of the total radiolabeled compound accounted for the unchanged parent drug [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 39 - 152 hours [2]
Metabolism: The drug is metabolized via the CYP2D6 and CYP3A4 [2]

Chemical Identifiers

Formula: C30H26F4N6O
IUPAC Name: 2-[3-(aminomethyl)phenyl]-N-[5-[(R)-(3-cyanophenyl)-(cyclopropylmethylamino)methyl]-2-fluorophenyl]-5-(trifluoromethyl)pyrazole-3-carboxamide
Canonical SMILES: C1CC1CN[C@@H](C2=CC(=C(C=C2)F)NC(=O)C3=CC(=NN3C4=CC=CC(=C4)CN)C(F)(F)F)C5=CC=CC(=C5)C#N
InChI: InChI=1S/C30H26F4N6O/c31-24-10-9-22(28(37-17-18-7-8-18)21-5-1-3-19(11-21)15-35)13-25(24)38-29(41)26-14-27(30(32,33)34)39-40(26)23-6-2-4-20(12-23)16-36/h1-6,9-14,18,28,37H,7-8,16-17,36H2,(H,38,41)/t28-/m1/s1
InChIKey: UXNXMBYCBRBRFD-MUUNZHRXSA-N

Cross-matching ID

PubChem CID: 137528262
CAS Number: 1809010-50-1
DrugBank ID: DB15982
TTD ID: DQ1S0B
ACDINA ID: D00877

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Plasma kallikrein (KLKB1)	TTMF8H9	KLKB1_HUMAN	Inhibitor	[1]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Crospovidone	E00626	Not Available	Disintegrant
Magnesium stearate	E00208	11177	lubricant
Hydrophobic colloidal silica	E00285	24261	Anticaking agent; Emulsion stabilizing agent; Glidant; Suspending agent; Viscosity-controlling agent
Pregelatinized starch	E00674	Not Available	Binding agent; Diluent; Disintegrant
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Berotralstat eq 110mg base capsule	eq 110mg base	Capsule	Oral
Berotralstat eq 150mg base capsule	eq 150mg base	Capsule	Oral

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References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health Human Services. 2020
2	FDA Approved Drug Products: ORLADEYO (berotralstat) capsules, for oral use