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Remimazolam Besylate

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Also known as: 308242-62-8, Cns 7056, Cns-7056, Ono-2745, 7v4a8u16mb, 308242-62-8 (freee base)

Molecular Formula

C₂₁H₁₉BrN₄O₂

Molecular Weight

439.3 g/mol

InChI Key

CYHWMBVXXDIZNZ-KRWDZBQOSA-N

FDA UNII

7V4A8U16MB

Remimazolam is a short-acting benzodiazepine derivative that is structurally related to midazolam, with sedative-hypnotic activity. Upon administration, remimazolam targets and binds to a specific site on the gamma-aminobutyric acid (GABA)-A-chloride ionophore receptor complex located on the neuronal membrane. Binding causes an allosteric modification of the receptor thereby enhancing the affinity of GABA to the receptor leading to an increase in the frequency of chloride-channel opening events, which leads to an increase in chloride ion conductance, neuronal hyperpolarization, inhibition of the action potential, and a decrease in neuronal excitability.

1 2D Structure

Remimazolam Besylate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

methyl 3-[(4S)-8-bromo-1-methyl-6-pyridin-2-yl-4H-imidazo[1,2-a][1,4]benzodiazepin-4-yl]propanoate

2.1.2 InChI

InChI=1S/C21H19BrN4O2/c1-13-12-24-21-17(7-9-19(27)28-2)25-20(16-5-3-4-10-23-16)15-11-14(22)6-8-18(15)26(13)21/h3-6,8,10-12,17H,7,9H2,1-2H3/t17-/m0/s1

2.1.3 InChI Key

CYHWMBVXXDIZNZ-KRWDZBQOSA-N

2.1.4 Canonical SMILES

CC1=CN=C2N1C3=C(C=C(C=C3)Br)C(=NC2CCC(=O)OC)C4=CC=CC=N4

2.1.5 Isomeric SMILES

CC1=CN=C2N1C3=C(C=C(C=C3)Br)C(=N[C@H]2CCC(=O)OC)C4=CC=CC=N4

2.2 Other Identifiers

2.2.1 UNII

7V4A8U16MB

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cns 7056

2. Methyl 3-(8-bromo-1-methyl-6-(2-pyridinyl)-4h-imidazo(1,2-a)(1,4)benzodiazepin-4-yl)propanoate

3. Ono 2745

4. Ono-2745

5. Ono2745

2.3.2 Depositor-Supplied Synonyms

1. 308242-62-8

2. Cns 7056

3. Cns-7056

4. Ono-2745

5. 7v4a8u16mb

6. 308242-62-8 (freee Base)

7. 4h-imidazo(1,2-a)(1,4)benzodiazepine-4-propanoic Acid, 8-bromo-1-methyl-6-(2-pyridinyl)-, Methyl Ester, (4s)-

8. Methyl (s)-3-(8-bromo-1-methyl-6-(pyridin-2-yl)-4h-benzo[f]imidazo[1,2-a][1,4]diazepin-4-yl)propanoate

9. Remimazolam [inn]

10. Unii-7v4a8u16mb

11. Remimazolam [mi]

12. Remimazolam (usan/inn)

13. Remimazolam [usan:inn]

14. Remimazolam [usan]

15. Remimazolam [who-dd]

16. Schembl846435

17. Chembl4297526

18. Dtxsid20953024

19. Ono2745

20. Amy15524

21. Ex-a5536

22. Ono 2745

23. Who 9232

24. Zinc3927450

25. Akos025213215

26. Db12404

27. Hy-14867

28. 4523b

29. Cs-0003605

30. D11788

31. 4h-imidazol(1,2-a)(1,4)benzodiazepine-4-propionic Acid, (s)-

32. (s)-methyl 3-(8-bromo-1-methyl-6-(pyridin-2-yl)-4h-benzo[f]imidazo[1,2-a][1,4]diazepin-4-yl)propanoate

33. Methyl 3-((4s)-8-bromo-1-methyl-6-(pyridin-2-yl)-4h-imidazo(1,2-a)(1,4)benzodiazepin-4-yl)propanoate

34. Methyl 3-[(4s)-8-bromo-1-methyl-6-(2-pyridyl)-4h-imidazo[1,2-a][1,4]benzodiazepin-4-yl]propanoate

35. Methyl 3-[(4s)-8-bromo-1-methyl-6-pyridin-2-yl-4h-imidazo[1,2-a][1,4]benzodiazepin-4-yl]propanoate

36. Methyl 3-[8-bromo-1-methyl-6-(pyridin-2-yl)-4h-imidazo[1,2-a][1,4]benzodiazepin-4-yl]propanoate

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₁₉BrN₄O₂
Molecular Weight	439.3 g/mol
XLogP3	3.4
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	5
Exact Mass	438.06914 g/mol
Monoisotopic Mass	438.06914 g/mol
Topological Polar Surface Area	69.4 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	601
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Remimazolam is indicated for the induction and maintenance of procedural sedation in adults undergoing procedures lasting 30 minutes or less.

FDA Label

Remimazolam is indicated in adults for procedural sedation.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Remimazolam modulates the effects of GABA(A) receptors in order to enhance the effects of GABA. It is considered an "ultra short-acting" benzodiazepine that achieves peak sedation within 3 to 3.5 minutes following intravenous administration, a property that makes it desirable for use during short procedures. Hepatic impairment can result in elevated serum levels of remimazolam - patients with severe hepatic impairment should be carefully titrated to effect. As of its approval date, remimazolam has not received a scheduling action by the DEA under the Controlled Substances Act. As benzodiazepines as a class have been implicated in the development of drug dependence and have a known potential for abuse, remimazolam should be used with caution in patients with a history of drug dependence or abuse.

5.2 ATC Code

N05CD

N - Nervous system

N05 - Psycholeptics

N05C - Hypnotics and sedatives

N05CD - Benzodiazepine derivatives

N05CD14 - Remimazolam

5.3 Absorption, Distribution and Excretion

Absorption

The C_max and AUC_0-inf following intravenous administration of 0.01 to 0.5 mg/kg were 189 to 6,960 ng/mL and 12.1 to 452 ngh/mL, respectively, and appear to be relatively dose proportional. The T_max of the inactive CNS7054 metabolite is approximately 20-30 minutes and its AUC_0-inf ranges from 231 to 7,090 ngh/mL.

Route of Elimination

In patients undergoing colonoscopy, approximately 0.003% of the administered dose is excreted in the urine as unchanged parent drug and 50-60% is excreted in the urine as CNS7054. In healthy subjects, >80% of the administered dose is excreted in the urine as CNS7054.

Volume of Distribution

The volume of distribution is approximately 0.76 - 0.98 L/kg.

Clearance

The clearance of remimazolam is approximately 24 - 75 L/h and is independent of body weight.

5.4 Metabolism/Metabolites

Remimazolam does not appear to undergo biotransformation via hepatic cytochrome P450 enzymes, nor does it induce or inhibit these enzymes. Its primary route of metabolism is hydrolysis via hepatic carboxylesterase-1 (CES1) to yield the inactive CNS7054 metabolite, which then undergoes glucuronidation and hydroxylation prior to elimination. CNS7054 possesses a 300-fold lesser affinity for GABA(A) receptors as compared to the parent drug.

5.5 Biological Half-Life

Following intravenous administration, the distribution half-life is of remimazolam is 0.5 - 2 minutes and the terminal elimination half-life is 37 - 53 minutes. Half-life is increased in patients with hepatic impairment necessitating careful dose titration in this population. The half-life of remimazolam's major inactive metabolite, CNS7054, is 2.4 - 3.8 hours.

5.6 Mechanism of Action

Like other benzodiazepines, remimazolam exerts its therapeutic effects by potentiating the effect of gamma-aminobutyric acid (GABA) on GABA(A) receptors, the main inhibitory neurotransmitter receptors in the mammalian brain. GABA(A) receptors are a component of GABA-gated ionotropic chloride channels that produce inhibitory postsynaptic potentials - following activation by GABA, the channel undergoes a conformational change that allows the passage of chloride ions through the channel. The inhibitory potentials produced by GABA neurotransmission play an integral role in the suppression and control of epileptiform nerve firing such as that seen in epilepsy, which makes the GABA system a desirable target in the treatment of epilepsy. Benzodiazepines are positive allosteric modulators of GABA(A) function. They bind to the interface between alpha () and gamma () subunits on the receptor, commonly referred to as the benzodiazepine binding site, and modulate the receptor such that its inhibitory response to GABA binding is dramatically increased.

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