Vericiguat

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H16F2N8O2
Molecular Weight	426.3795
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

COC(=O)NC1=C(N)N=C(N=C1N)C2=NN(CC3=CC=CC=C3F)C4=NC=C(F)C=C24

InChI

InChIKey=QZFHIXARHDBPBY-UHFFFAOYSA-N

InChI=1S/C19H16F2N8O2/c1-31-19(30)25-14-15(22)26-17(27-16(14)23)13-11-6-10(20)7-24-18(11)29(28-13)8-9-4-2-3-5-12(9)21/h2-7H,8H2,1H3,(H,25,30)(H4,22,23,26,27)

HIDE SMILES / InChI

Molecular Formula	C19H16F2N8O2
Molecular Weight	426.3795
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

Vericiguat, discovered at Bayer, is the first soluble guanylate cyclase (sGC) stimulator. Vericiguat is currently being studied in a Phase III clinical program for the treatment of heart failure with reduced ejection fraction (HFrEF).

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Soluble guanylate cyclase 36	Activator 1,447		1005.0 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Heart Failure 7	Primary		Phase III 665	Unknown

C_max

Value	Dose	Analyte	Population
350 μg/L	10 mg 1 times / day steady-state, oral	VERICIGUAT plasma	Homo sapiens
41 μg/L	1.25 mg single, oral	VERICIGUAT plasma	Homo sapiens
106 μg/L	5 mg single, oral	VERICIGUAT plasma	Homo sapiens
176 μg/L	5 mg single, oral	VERICIGUAT plasma	Homo sapiens
115 μg/L	5 mg single, oral	VERICIGUAT plasma	Homo sapiens
72 μg/L	2.5 mg single, oral	VERICIGUAT plasma	Homo sapiens
129 μg/L	5 mg single, oral	VERICIGUAT plasma	Homo sapiens
279 μg/L	10 mg single, oral	VERICIGUAT plasma	Homo sapiens
202 μg/L	10 mg single, oral	VERICIGUAT plasma	Homo sapiens
274 μg/L	10 mg single, oral	VERICIGUAT plasma	Homo sapiens
195 μg/L	10 mg single, oral	VERICIGUAT plasma	Homo sapiens
61.8 μg/L	1.25 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
236 μg/L	5 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
324 μg/L	7.5 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
365 μg/L	10 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
46.4 μg/L	1.25 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
161 μg/L	5 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
242 μg/L	7.5 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
285 μg/L	10 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
89.2 μg/L	1.25 mg 1 times / day steady-state, oral	VERICIGUAT plasma	Homo sapiens
289 μg/L	5 mg 1 times / day steady-state, oral	VERICIGUAT plasma	Homo sapiens
407 μg/L	7.5 mg 1 times / day steady-state, oral	VERICIGUAT plasma	Homo sapiens
472 μg/L	10 mg 1 times / day steady-state, oral	VERICIGUAT plasma	Homo sapiens
17.2 μg/L	0.5 mg single, oral	VERICIGUAT plasma	Homo sapiens
39.3 μg/L	1 mg single, oral	VERICIGUAT plasma	Homo sapiens
82.7 μg/L	2.5 mg single, oral	VERICIGUAT plasma	Homo sapiens
158 μg/L	5 mg single, oral	VERICIGUAT plasma	Homo sapiens
194 μg/L	5 mg single, oral	VERICIGUAT plasma	Homo sapiens
259 μg/L	7.5 mg single, oral	VERICIGUAT plasma	Homo sapiens
285 μg/L	10 mg single, oral	VERICIGUAT plasma	Homo sapiens
430 μg/L	15 mg single, oral	VERICIGUAT plasma	Homo sapiens
38.5 μg/L	1.25 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
114 μg/L	5 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
200 μg/L	10 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
136 μg/L	5 mg 2 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
51.4 μg/L	1.25 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
185 μg/L	5 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
310 μg/L	10 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
312 μg/L	5 mg 2 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
83.1 μg/L	2.5 mg single, oral	VERICIGUAT plasma	Homo sapiens
76.2 μg/L	2.5 mg single, oral	VERICIGUAT plasma	Homo sapiens
92.7 μg/L	2.5 mg single, oral	VERICIGUAT plasma	Homo sapiens
91.4 μg/L	2.5 mg single, oral	VERICIGUAT plasma	Homo sapiens
66.6 μg/L	2.5 mg single, oral	VERICIGUAT plasma	Homo sapiens
69.5 μg/L	2.5 mg single, oral	VERICIGUAT plasma	Homo sapiens
68.7 μg/L	2.5 mg single, oral	VERICIGUAT plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
6680 μg × h/mL	10 mg 1 times / day steady-state, oral	VERICIGUAT plasma	Homo sapiens
754 μg × h/L	1.25 mg single, oral	VERICIGUAT plasma	Homo sapiens
2300 μg × h/L	5 mg single, oral	VERICIGUAT plasma	Homo sapiens
3260 μg × h/L	5 mg single, oral	VERICIGUAT plasma	Homo sapiens
2730 μg × h/L	5 mg single, oral	VERICIGUAT plasma	Homo sapiens
1360 μg × h/L	2.5 mg single, oral	VERICIGUAT plasma	Homo sapiens
2520 μg × h/L	5 mg single, oral	VERICIGUAT plasma	Homo sapiens
5480 μg × h/L	10 mg single, oral	VERICIGUAT plasma	Homo sapiens
3890 μg × h/L	10 mg single, oral	VERICIGUAT plasma	Homo sapiens
5600 μg × h/L	10 mg single, oral	VERICIGUAT plasma	Homo sapiens
3890 μg × h/L	10 mg single, oral	VERICIGUAT plasma	Homo sapiens
703 μg × h/L	1.25 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
2540 μg × h/L	5 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
3230 μg × h/L	7.5 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
4410 μg × h/L	10 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
666 μg × h/L	1.25 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
2370 μg × h/L	5 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
3300 μg × h/L	7.5 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
4340 μg × h/L	10 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
1170 μg × h/L	1.25 mg 1 times / day steady-state, oral	VERICIGUAT plasma	Homo sapiens
3670 μg × h/L	5 mg 1 times / day steady-state, oral	VERICIGUAT plasma	Homo sapiens
4810 μg × h/L	7.5 mg 1 times / day steady-state, oral	VERICIGUAT plasma	Homo sapiens
6170 μg × h/L	10 mg 1 times / day steady-state, oral	VERICIGUAT plasma	Homo sapiens
273 μg × h/L	0.5 mg single, oral	VERICIGUAT plasma	Homo sapiens
618 μg × h/L	1 mg single, oral	VERICIGUAT plasma	Homo sapiens
1450 μg × h/L	2.5 mg single, oral	VERICIGUAT plasma	Homo sapiens
2900 μg × h/L	5 mg single, oral	VERICIGUAT plasma	Homo sapiens
2500 μg × h/L	5 mg single, oral	VERICIGUAT plasma	Homo sapiens
4460 μg × h/L	7.5 mg single, oral	VERICIGUAT plasma	Homo sapiens
4940 μg × h/L	10 mg single, oral	VERICIGUAT plasma	Homo sapiens
7900 μg × h/L	15 mg single, oral	VERICIGUAT plasma	Homo sapiens
423 μg × h/L	1.25 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
1370 μg × h/L	5 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
2240 μg × h/L	10 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
951 μg × h/L	5 mg 2 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
656 μg × h/L	1.25 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
2230 μg × h/L	5 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
3840 μg × h/L	10 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
2600 μg × h/L	5 mg 2 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
1330 μg × h/L	2.5 mg single, oral	VERICIGUAT plasma	Homo sapiens
1390 μg × h/L	2.5 mg single, oral	VERICIGUAT plasma	Homo sapiens
2200 μg × h/L	2.5 mg single, oral	VERICIGUAT plasma	Homo sapiens
2940 μg × h/L	2.5 mg single, oral	VERICIGUAT plasma	Homo sapiens
1550 μg × h/L	2.5 mg single, oral	VERICIGUAT plasma	Homo sapiens
1780 μg × h/L	2.5 mg single, oral	VERICIGUAT plasma	Homo sapiens
1250 μg × h/L	2.5 mg single, oral	VERICIGUAT plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
20 h	10 mg 1 times / day steady-state, oral	VERICIGUAT plasma	Homo sapiens
18.8 h	1.25 mg single, oral	VERICIGUAT plasma	Homo sapiens
20.4 h	5 mg single, oral	VERICIGUAT plasma	Homo sapiens
21.4 h	5 mg single, oral	VERICIGUAT plasma	Homo sapiens
18.9 h	5 mg single, oral	VERICIGUAT plasma	Homo sapiens
18.5 h	2.5 mg single, oral	VERICIGUAT plasma	Homo sapiens
18.1 h	5 mg single, oral	VERICIGUAT plasma	Homo sapiens
17.6 h	10 mg single, oral	VERICIGUAT plasma	Homo sapiens
18.2 h	10 mg single, oral	VERICIGUAT plasma	Homo sapiens
18 h	10 mg single, oral	VERICIGUAT plasma	Homo sapiens
18.9 h	10 mg single, oral	VERICIGUAT plasma	Homo sapiens
22.3 h	1.25 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
21.1 h	5 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
17.9 h	7.5 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
18.3 h	10 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
27 h	1.25 mg 1 times / day steady-state, oral	VERICIGUAT plasma	Homo sapiens
23.5 h	5 mg 1 times / day steady-state, oral	VERICIGUAT plasma	Homo sapiens
22.1 h	7.5 mg 1 times / day steady-state, oral	VERICIGUAT plasma	Homo sapiens
20.7 h	10 mg 1 times / day steady-state, oral	VERICIGUAT plasma	Homo sapiens
17.2 h	0.5 mg single, oral	VERICIGUAT plasma	Homo sapiens
19.4 h	1 mg single, oral	VERICIGUAT plasma	Homo sapiens
19.4 h	2.5 mg single, oral	VERICIGUAT plasma	Homo sapiens
19.8 h	5 mg single, oral	VERICIGUAT plasma	Homo sapiens
14.5 h	5 mg single, oral	VERICIGUAT plasma	Homo sapiens
19.8 h	7.5 mg single, oral	VERICIGUAT plasma	Homo sapiens
20.7 h	10 mg single, oral	VERICIGUAT plasma	Homo sapiens
17.2 h	15 mg single, oral	VERICIGUAT plasma	Homo sapiens
25.7 h	1.25 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
24.7 h	5 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
19.9 h	10 mg 1 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
20.7 h	5 mg 2 times / day multiple, oral	VERICIGUAT plasma	Homo sapiens
20.7 h	2.5 mg single, oral	VERICIGUAT plasma	Homo sapiens
17.1 h	2.5 mg single, oral	VERICIGUAT plasma	Homo sapiens
32.1 h	2.5 mg single, oral	VERICIGUAT plasma	Homo sapiens
36.9 h	2.5 mg single, oral	VERICIGUAT plasma	Homo sapiens
19.8 h	2.5 mg single, oral	VERICIGUAT plasma	Homo sapiens
23.7 h	2.5 mg single, oral	VERICIGUAT plasma	Homo sapiens
20.2 h	2.5 mg single, oral	VERICIGUAT plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
2%			VERICIGUAT plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
10 mg 1 times / day multiple, oral Recommended	unhealthy, ADULT	Disc. AE: Embryo-fetal toxicity...
10 mg 1 times / day multiple, oral Recommended	unhealthy, ADULT	Other AEs: Hypotension, Syncope...

Showing 1 to 2 of 2 entries

Previous1Next

AEs

Show entries

AE	Significance	Dose	Population
Embryo-fetal toxicity	Disc. AE	10 mg 1 times / day multiple, oral Recommended	unhealthy, ADULT
Hypotension	15.4%	10 mg 1 times / day multiple, oral Recommended	unhealthy, ADULT
Syncope	4.4%	10 mg 1 times / day multiple, oral Recommended	unhealthy, ADULT

Showing 1 to 3 of 3 entries

Previous1Next

PubMed

Show entries

Title	Date	PubMed
Discovery of the Soluble Guanylate Cyclase Stimulator Vericiguat (BAY 1021189) for the Treatment of Chronic Heart Failure.	2017 Jun 22	28557445

Showing 1 to 1 of 1 entries

Previous1Next

Patents

Sample Use Guides

In Vivo Use Guide

Starting dose of 2.5 mg taken orally once daily with food, on a background of standard of care. Dose will be uptitrated to 5 mg and to 10 mg.

Route of Administration: Oral

In Vitro Use Guide

Studies on the in vitro effects of Vericiguat on highly purified sGC (soluble guanylate cyclase) revealed that Vericiguat (0.01 uM to 100 uM) stimulates recombinant sGC concentration dependently, by 1.7-fold to 57.6-fold.

Substance Class	Chemical
Record UNII	LV66ADM269
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

Vericiguat [INN]

Preferred Name

English

Vericiguat

Official Name

English

Methyl N-[4,6-diamino-2-[5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl]carbamate

Systematic Name

English

Methyl (4,6-diamino-2-(5-fluoro-1-((2-fluorophenyl)methyl)-1H-pyrazolo(3,4-b)pyridin-3-yl(pyrimidin-5-yl)carbamate

Systematic Name

English

Methyl [4,6-diamino-2-[5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl]carbamate

Systematic Name

English

Showing 1 to 5 of 13 entries

Previous1 2 3Next

Show entries

Classification Tree

Code System

Code

Agent Affecting Cardiovascular System

NCI_THESAURUS

C29707

Showing 1 to 1 of 1 entries

Previous1Next

Show entries

Code System

Code

Type

Description

FDA UNII

LV66ADM269

PRIMARY

WIKIPEDIA

Vericiguat

PRIMARY

CHEBI

142432

PRIMARY

INN

9805

PRIMARY

DRUG BANK

DB15456

PRIMARY

Showing 1 to 5 of 13 entries

Previous1 2 3Next

Show entries

Related Record

Type

Details


					5G76IGF54K

VERICIGUAT HYDROCHLORIDE

SALT/SOLVATE -> PARENT

Amount:


					76UB6O122H

ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2

TRANSPORTER -> SUBSTRATE

Amount:


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Comments:

Protein binding (primarily to serum albumin) of vericiguat is about 98%.

Interaction Type:

BINDING

Amount:

98 % (average)


					22ES734693

MULTIDRUG RESISTANCE PROTEIN 1

TRANSPORTER -> SUBSTRATE

Amount:


					0RFO7VC96N

URIDINE DIPHOSPHATE GLUCURONOSYLTRANSFERASE 1A1

METABOLIC ENZYME -> SUBSTRATE

Amount:

Showing 1 to 5 of 7 entries

Previous1 2Next

Show entries

Related Record

Type

Details


					LV66ADM269

Vericiguat

ACTIVE MOIETY

Amount:

Showing 1 to 1 of 1 entries

Previous1Next

Name	Property Type	Amount	Referenced Substance	Parameters
Volume of Distribution	PHARMACOKINETIC	44 LITERS (average)	`LV66ADM269` Vericiguat	IN HEALTHY SUBJECTS PHARMACOKINETIC

Tmax	PHARMACOKINETIC	1 hours (average)	`LV66ADM269` Vericiguat	FASTED STATE PHARMACOKINETIC

ABSOLUTE BIOAVAILABILITY	PHARMACOKINETIC	93 % (average)	`LV66ADM269` Vericiguat	FED CONDITION PHARMACOKINETIC

Biological Half-life	PHARMACOKINETIC	30 hours (average)	`LV66ADM269` Vericiguat	IN PATIENTS WITH HEART FAILURE NUCLEIC ACID FEATURE

Tmax	PHARMACOKINETIC	4 hours (average)	`LV66ADM269` Vericiguat	HIGH-FAT, HIGH-CALORIE MEAL PHARMACOKINETIC

SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound