CABOTEGRAVIR SODIUM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H16F2N3O5.Na
Molecular Weight	427.334
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].C[C@H]1CO[C@@H]2CN3C=C(C(=O)NCC4=CC=C(F)C=C4F)C(=O)C([O-])=C3C(=O)N12

InChI

InChIKey=AEZBWGMXBKPGFP-KIUAEZIZSA-M

InChI=1S/C19H17F2N3O5.Na/c1-9-8-29-14-7-23-6-12(16(25)17(26)15(23)19(28)24(9)14)18(27)22-5-10-2-3-11(20)4-13(10)21;/h2-4,6,9,14,26H,5,7-8H2,1H3,(H,22,27);/q;+1/p-1/t9-,14+;/m0./s1

HIDE SMILES / InChI

Molecular Formula	C19H16F2N3O5
Molecular Weight	404.3442
Charge	-1
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	Na
Molecular Weight	22.98976928
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://aidsinfo.nih.gov/drugs/513/cabotegravir/0/patient
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27799824

Cabotegravir is an investigational drug that is being studied for the treatment and prevention of HIV infection. Cabotegravir belongs to a class (group) of HIV drugs called integrase inhibitors. Integrase inhibitors block an HIV enzyme called integrase. (An enzyme is a protein that starts or increases the speed of a chemical reaction.) By blocking integrase, integrase inhibitors prevent HIV from multiplying and can reduce the amount of HIV in the body. Cabotegravir does not require boosting with an additional drug. Two forms of cabotegravir are being studied: tablets that are taken by mouth (known as oral cabotegravir or oral CAB) and a long-acting injectable form that is injected into the muscle (known as cabotegravir LA or CAB LA; LA stands for "long-acting"). (A long-acting drug formulation works over a long period of time. Using this type of drug might mean that the drug could be taken less often, making a treatment or prevention regimen simpler to take.) Cabotegravir is in Phase-III clinical trials for HIV infections.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Human immunodeficiency virus 1 34 Target ID: CHEMBL378 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23845180	Inhibitor 8504	0.2 nM [IC50]
Solute carrier family 22 member 6 19 Target ID: CHEMBL1641347 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26340566	Inhibitor 8504	0.81 µM [IC50]
Solute carrier family 22 member 8 17 Target ID: CHEMBL1641348 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26340566	Inhibitor 8504	0.41 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
HIV-1 infection 156 Sources: https://aidsinfo.nih.gov/drugs/513/cabotegravir/0/professional	Primary		Phase III 665	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
3.61 μg/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/28739783/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		CABOTEGRAVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
3.39 μg/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/28739783/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: RIFAMPIN	RIFAMPIN	CABOTEGRAVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
3.4 μg/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/30809978/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		CABOTEGRAVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
3.44 μg/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/30809978/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		CABOTEGRAVIR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
146 μg × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/28739783/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		CABOTEGRAVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
59.7 μg × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/28739783/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: RIFAMPIN	RIFAMPIN	CABOTEGRAVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
144 μg × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/30809978/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		CABOTEGRAVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
146 μg × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/30809978/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		CABOTEGRAVIR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
38.5 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/28739783/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		CABOTEGRAVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
16.4 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/28739783/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: RIFAMPIN	RIFAMPIN	CABOTEGRAVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
40.8 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/30809978/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		CABOTEGRAVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
39.6 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/30809978/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		CABOTEGRAVIR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
0.12% CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/30809978/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		CABOTEGRAVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
0.17% CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/30809978/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		CABOTEGRAVIR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Doses

Dose	Population	Adverse events
50 mg single, oral Higher than recommended Dose: 50 mg Route: oral Route: single Dose: 50 mg Sources: https://pubmed.ncbi.nlm.nih.gov/24144896/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/24144896/	Sources: https://pubmed.ncbi.nlm.nih.gov/24144896/
800 mg 1 times / 3 months multiple, intramuscular Higher than recommended Dose: 800 mg, 1 times / 3 months Route: intramuscular Route: multiple Dose: 800 mg, 1 times / 3 months Sources: https://pubmed.ncbi.nlm.nih.gov/28546090/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/28546090/	Disc. AE: Injection site pain... AEs leading to discontinuation/dose reduction: Injection site pain (4%) Sources: https://pubmed.ncbi.nlm.nih.gov/28546090/
30 mg single, oral Recommended Dose: 30 mg Route: oral Route: single Dose: 30 mg Sources: https://pubmed.ncbi.nlm.nih.gov/30230694/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/30230694/	Sources: https://pubmed.ncbi.nlm.nih.gov/30230694/
600 mg 1 times / 2 months multiple, intramuscular Dose: 600 mg, 1 times / 2 months Route: intramuscular Route: multiple Dose: 600 mg, 1 times / 2 months Sources: https://pubmed.ncbi.nlm.nih.gov/28750935/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/28750935/	Disc. AE: Injection site pain... AEs leading to discontinuation/dose reduction: Injection site pain (1.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/28750935/
30 mg 1 times / day multiple, oral Recommended Dose: 30 mg, 1 times / day Route: oral Route: multiple Dose: 30 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/24144896/	healthy Health Status: healthy Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/24144896/	Sources: https://pubmed.ncbi.nlm.nih.gov/24144896/

AEs

AE	Significance	Dose	Population
Injection site pain	4% Disc. AE	800 mg 1 times / 3 months multiple, intramuscular Higher than recommended Dose: 800 mg, 1 times / 3 months Route: intramuscular Route: multiple Dose: 800 mg, 1 times / 3 months Sources: https://pubmed.ncbi.nlm.nih.gov/28546090/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/28546090/
Injection site pain	1.7% Disc. AE	600 mg 1 times / 2 months multiple, intramuscular Dose: 600 mg, 1 times / 2 months Route: intramuscular Route: multiple Dose: 600 mg, 1 times / 2 months Sources: https://pubmed.ncbi.nlm.nih.gov/28750935/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/28750935/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 inducer 1087	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2A6 879 P-gp 1741 UGT2B7 197 UGT1A3 89 UGT1A6 136 BCRP 910 OATP1B3 961 UGT2B4 23 CYP2B6 926 OCT1 620 CYP2C19 2057 UGT2B17 31 CYP1A2 2153 UGT1A4 98 BSEP 550 CYP2C8 1057 UGT1A9 148 UGT2B15 84 UGT1A1 246 OATP1B1 1079 OCT2 779 MATE1 415 MATE2-K 77 MRP2 499 MRP4 290 OAT3 747 OAT1 725	UGT1A9 423 OATP1B3 435 UGT1A1 479 OCT1 393 P-gp 2052 BCRP 697 OATP1B1 503	CYP1A2 832 CYP2B6 669

Drug as perpetrator

Target	Modality	Activity
BCRP 985	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
BSEP 554	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
CYP1A2 2333	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
CYP2A6 911	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
CYP2B6 1160	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
CYP3A4 2633	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
MATE1 416	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
MATE2-K 77	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
MRP2 625	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
MRP4 345	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
OATP1B1 1095	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
OATP1B3 970	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
OCT1 656	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
OCT2 782	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
P-gp 1932	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
UGT1A1 303	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
UGT1A3 99	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
UGT1A4 100	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
UGT1A6 171	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
UGT1A9 155	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
UGT2B15 84	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
UGT2B17 33	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
UGT2B4 23	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
UGT2B7 210	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
OAT3 749	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf#page=38 \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2023/215499s002lbl.pdf#page=23 Page: 38.0	yes [IC50 0.41 uM]
OAT1 730	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf#page=38 \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2023/215499s002lbl.pdf#page=23 Page: 38.0	yes [IC50 0.81 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
UGT1A1 479	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf#page=38 \| https://pubmed.ncbi.nlm.nih.gov/32361755/ Page: 38.0	major	yes (pharmacogenomic study) Comment: Statistically significant (P < 0.05) associations were observed between UGT1A1 genotype and plasma cabotegravir PK parameters, with 28%–50% increases following oral cabotegravir [plasma cabotegravir concentration at the end of the dosing interval (Ctau), 1.50-fold; AUCtau, 1.41-fold; and Cmax, 1.28-fold] and 16%– 24% increases following cabotegravir LA administration (48 week Ctau, 1.24-fold; AUCtau, 1.16-fold; and Cmax, 1.18-fold) among those with low-versus-normal genetically predicted UGT1A1 activity. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf#page=38 \| https://pubmed.ncbi.nlm.nih.gov/32361755/ Page: 38.0
UGT1A9 423	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	minor
OATP1B1 503	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
OATP1B3 435	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
OCT1 393	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	no
BCRP 697	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	yes
P-gp 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215499Orig1s000IntegratedR.pdf Page: 38.0	yes

PubMed

Title	Date	PubMed
Effect of Cabotegravir on Cardiac Repolarization in Healthy Subjects.	2016-11	27162089
Profile of cabotegravir and its potential in the treatment and prevention of HIV-1 infection: evidence to date.	2016	27799824

Patents

Sample Use Guides

In Vivo Use Guide

10, 30, or 60 mg once daily

Route of Administration: Oral

In Vitro Use Guide

Cabotegravir (GSK1265744) inhibited HIV replication with low or subnanomolar efficacy, it inhibited the HIV-1 integrase catalyzed strand transfer reaction with an IC50 of 3.0 nM in vitro. The antiviral EC50 against HIV-1 Ba-L was 0.22 nM, and that against NL432 was 0.34 nM in PBMCs, 0.57 nM using CellTiter-Glo and 1.3 nM using MTT in MT-4 cells, and 0.5 nM in the PHIV assay, which uses a pseudotyped self-inactivating virus.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:50:17 GMT 2025` Edited by `admin` on `Mon Mar 31 22:50:17 GMT 2025`
Record UNII	3L12PT535M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GSK-1265744B

Preferred Name

English

CABOTEGRAVIR SODIUM

Official Name

English

Cabotegravir sodium [WHO-DD]

Common Name

English

CABOTEGRAVIR SODIUM [ORANGE BOOK]

Common Name

English

GSK1265744B

Code

English

VOCABRIA

Brand Name

English

Sodium (3S,11aR)-8-{[(2,4-difluorophenyl)methyl]carbamoyl}-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydrooxazolo[3,2-a]pyrido[1,2-d]pyrazin-6-olate

Systematic Name

English

CABOTEGRAVIR SODIUM [JAN]

Common Name

English

CABOTEGRAVIR SODIUM [USAN]

Common Name

English

S-265744B

Code

English

OXAZOLO(3,2-A)PYRIDO(1,2-D)PYRAZINE-8-CARBOXAMIDE, N-((2,4-DIFLUOROPHENYL)METHYL)-2,3,5,7,11,11A-HEXAHYDRO-6-HYDROXY-3-METHYL-5,7-DIOXO-, SODIUM SALT (1:1), (3S,11AR)-

Systematic Name

English

Code System Code Type Description

DAILYMED

3L12PT535M