COBALT PROTOPORPHYRIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C34H32N4O4.Co
Molecular Weight	619.5755
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Co++].CC1=C2NC(C=C3N=C(C=C4NC(=CC5=NC(=C2)C(C=C)=C5C)C(C=C)=C4C)C(C)=C3CCC([O-])=O)=C1CCC([O-])=O

InChI

InChIKey=PZVPSKRBVYHPFM-RGGAHWMASA-L

InChI=1S/C34H34N4O4.Co/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25;/h7-8,13-16,35,38H,1-2,9-12H2,3-6H3,(H,39,40)(H,41,42);/q;+2/p-2/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;

HIDE SMILES / InChI

Molecular Formula	Co
Molecular Weight	58.933195
Charge	2
Count

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

Molecular Formula	C34H32N4O4
Molecular Weight	560.6423
Charge	-2
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26255181 | https://www.ncbi.nlm.nih.gov/pubmed/15059790 | https://www.ncbi.nlm.nih.gov/pubmed/24255720

Cobalt protoporphyrin (CoPP) is a potent HO-1 inducer and generally known to be an antioxidant in various cell types. CoPP has been shown to downregulate various cytochrome P450 isoforms, and various mechanisms of action have been attributed to its ability to induced HO- 1. It has also been used to promote endogenous carbon dioxide (CO) generation and protect against myocardial infarction in vivo. CoPP also participated in regulating the inflammatory response in CNS which mainly suppressed inflammatory component. It has been demonstrated that CoPP reduced LPS/Interleukin 13 (IL-13)-induced microglial death.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase-2 201 Target ID: CHEMBL4321 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26255181	Activator 1447
Heme oxygenase 1 15 Target ID: CHEMBL4434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26255181	Activator 1447

Conditions

Condition	Modality	Highest Phase	Product
Uremic cardiomyopathy 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27698370	Primary	Preclinical	Unknown Approved Use Unknown
Dengue virus infection 12 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27553177	Primary	Basic research	Unknown Approved Use Unknown
Diabetic neuropathy 23 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26762785 https://www.ncbi.nlm.nih.gov/pubmed/26730587	Primary	Preclinical	Unknown Approved Use Unknown
Neuropathic pain 26 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26361083	Palliative	Preclinical	Unknown Approved Use Unknown
Obesity 206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26681956 https://www.ncbi.nlm.nih.gov/pubmed/26026874 https://www.ncbi.nlm.nih.gov/pubmed/21467998	Primary	Preclinical	Unknown Approved Use Unknown
Glaucoma 57 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24799032	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Heme and heme biosynthesis intermediates induce heme oxygenase-1 and cytochrome P450 2A5, enzymes with putative sequential roles in heme and bilirubin metabolism: different requirement for transcription factor nuclear factor erythroid- derived 2-like 2.	2012-11	22859313
Oxidative stress fuels Trypanosoma cruzi infection in mice.	2012-07	22728935
Heme oxygenase-1 promotes the persistence of Leishmania chagasi infection.	2012-05-01	22461696
High-fat diet exacerbates renal dysfunction in SHR: reversal by induction of HO-1-adiponectin axis.	2012-05	22193921
Heme oxygenase-1 is protective against nonsteroidal anti-inflammatory drug-induced gastric ulcers.	2012-04	21873894
Induction of heme oxygenase-1 shifts the balance from proinjury to prosurvival in the placentas of pregnant rats with reduced uterine perfusion pressure.	2012-03-01	22237591
Haem oxygenase-1 counteracts the effects of interleukin-1β on inflammatory and senescence markers in cartilage-subchondral bone explants from osteoarthritic patients.	2012-03	21954917
Heme oxygenase-1 mediates protective effects on inflammatory, catabolic and senescence responses induced by interleukin-1β in osteoarthritic osteoblasts.	2012-02-01	22155307
Carbon monoxide reduces neuropathic pain and spinal microglial activation by inhibiting nitric oxide synthesis in mice.	2012	22928017
Cobalt-Protoporphyrin Improves Heart Function by Blunting Oxidative Stress and Restoring NO Synthase Equilibrium in an Animal Model of Experimental Diabetes.	2012	22675305
Dimethylsulfoxide (DMSO) induces downregulation of heme oxygenase-1 (HO-1) in HL-60 cells: involvement of HO-1 in HL-60 cell differentiation.	2011-11	22118543
Protective Effect of Heme Oxygenase-1 on High Glucose-Induced Pancreatic β-Cell Injury.	2011-10	22111038
Hemo oxygenase-1 induction in vitro and in vivo can yield pancreas islet xenograft survival and improve islet function.	2011-10	22088539
Inhibition of heme oxygenase-1 enhances anti-cancer effects of arsenic trioxide on glioma cells.	2011-09	21327864
An anti-inflammatory role for carbon monoxide and heme oxygenase-1 in chronic Th2-mediated murine colitis.	2011-05-01	21444764
Induction of heme oxygenase-1 expression by cilostazol contributes to its anti-inflammatory effects in J774 murine macrophages.	2011-05	21256160
Ectopic overexpression of haem oxygenase-1 protects kidneys from carboplatin-mediated apoptosis.	2011-04	21198546
Preconditioning with cobalt protoporphyrin protects human gastric mucosal cells from deoxycholate-induced apoptosis.	2011-03-03	21362092
Effects of heme oxygenase-1 on pulmonary function and structure in rats with liver cirrhosis.	2011-03	21518603
Heme oxygenase regulates renal arterial resistance and sodium excretion in cirrhotic rats.	2011-02	21055838
Effect of heme oxygenase-1 on renal function in rats with liver cirrhosis.	2011-01-21	21253390
Heme oxygenase-1 induction restores high-blood-flow-dependent remodeling and endothelial function in mesenteric arteries of old rats.	2011-01	20935577
Protective effect of heme oxygenase-1 to pancreas islet xenograft.	2010-12	20056245
Heme oxygenase-1 regulates the major route involved in formation of immune hepatic fibrosis in rats.	2010-11	21163135
Induction of hemeoxygenase-1 attenuates the hypertension and renal inflammation in spontaneously hypertensive rats.	2010-11	20667508
DMF inhibits PDGF-BB induced airway smooth muscle cell proliferation through induction of heme-oxygenase-1.	2010-10-20	20961405
Adiponectin and heme oxygenase-1 suppress TLR4/MyD88-independent signaling in rat Kupffer cells and in mice after chronic ethanol exposure.	2010-10-15	20861358
[Effect of cobalt protoporphyrin on hyperexpression of heme oxygenase-1 and secretion of IL-10 in rat bone marrow mesenchymal stem cells].	2010-10	21129280
Epigallocatechin gallate-mediated protection against tumor necrosis factor-α-induced monocyte chemoattractant protein-1 expression is heme oxygenase-1 dependent.	2010-10	20580034
Retinal protection from acute glaucoma-induced ischemia-reperfusion injury through pharmacologic induction of heme oxygenase-1.	2010-09	20357190
Neferine inhibits angiotensin II-stimulated proliferation in vascular smooth muscle cells through heme oxygenase-1.	2010-06	20523338
In vivo inhibition of renal heme oxygenase with an imidazole-dioxolane inhibitor.	2010-06	20338241
Arsenite down-regulates cytochrome P450 1A1 at the transcriptional and posttranslational levels in human HepG2 cells.	2010-05-15	20188822
Haem oxygenase-1 down-regulates high mobility group box 1 and matrix metalloproteinases in osteoarthritic synoviocytes.	2010-05	20110250
Overexpression of heme oxygenase-1 increases human osteoblast stem cell differentiation.	2010-05	19924377
Heme Oxygenase-1 expression in M-CSF-polarized M2 macrophages contributes to LPS-induced IL-10 release.	2010-04-22	20580464
The anti-inflammatory effects of adiponectin are mediated via a heme oxygenase-1-dependent pathway in rat Kupffer cells.	2010-04	20052772
Cilostazol enhances apoptosis of synovial cells from rheumatoid arthritis patients with inhibition of cytokine formation via Nrf2-linked heme oxygenase 1 induction.	2010-03	20131233
Effects of losartan, HO-1 inducers or HO-1 inhibitors on erectile signaling in diabetic rats.	2009-12	19804535
Methamphetamine induces heme oxygenase-1 expression in cortical neurons and glia to prevent its toxicity.	2009-11-01	19576919
Overexpression of HO-1 protects against TNF-alpha-mediated airway inflammation by down-regulation of TNFR1-dependent oxidative stress.	2009-08	19608869
Cobalt protoporphyrin inhibition of lipopolysaccharide or lipoteichoic acid-induced nitric oxide production via blocking c-Jun N-terminal kinase activation and nitric oxide enzyme activity.	2009-07-15	19497418
Influence of heme oxygenase-1 expression on immune liver fibrosis induced by cobalt protoporphyrin in rats.	2009-06-28	19554654
Heme oxygenase-1 induction modulates microsomal prostaglandin E synthase-1 expression and prostaglandin E(2) production in osteoarthritic chondrocytes.	2009-06-15	19428335
Role for copper in the cellular and regulatory effects of heme-hemopexin.	2009-06	19039664
A phosphodiesterase III inhibitor protects rat liver from sinusoidal obstruction syndrome through heme oxygenase-1 induction.	2009-05	19387321
15-Deoxy-Delta12,14-prostaglandin J2 upregulates the expression of heme oxygenase-1 and subsequently matrix metalloproteinase-1 in human breast cancer cells: possible roles of iron and ROS.	2009-04	19136476
Heme-oxygenase induction inhibits arteriolar thrombosis in vivo: effect of the non-substrate inducer cobalt protoporphyrin.	2009-03-15	19168058
Heme oxygenase-1 induction remodels adipose tissue and improves insulin sensitivity in obesity-induced diabetic rats.	2009-03	19171794
Heme oxygenase-derived carbon monoxide restores vascular function in type 1 diabetes.	2008-12	19356108

Patents

Sample Use Guides

In Vivo Use Guide

Mice: repeated intraperitoneal administration of Cobalt protoporphyrin (5 mg/kg/d) significantly reduced the mechanical allodynia and thermal hyperalgesia induced by SNL

Route of Administration: Intraperitoneal

In Vitro Use Guide

Cobalt protoporphyrin (CoPP) (0.5, 1, or 2 uM) upregulates COX-2 and HO-1 expression in BV-2 microglial cells.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:29:30 GMT 2025` Edited by `admin` on `Mon Mar 31 21:29:30 GMT 2025`
Record UNII	63AAN3JDZE
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

COBALT PROTOPORPHYRIN

Common Name

English

NSC-267101

Preferred Name

English

COBALTATE(2-), (7,12-DIETHENYL-3,8,13,17-TETRAMETHYL-21H,23H-PORPHINE-2,18-DIPROPANOATO(4-)-.KAPPA.N21,.KAPPA.N22,.KAPPA.N23,.KAPPA.N24)-, DIHYDROGEN, (SP-4-2)-

Common Name

English

COBALT PROTOPORPHYRIN IX

Common Name

English

COBALTATE(2-), (7,12-DIETHENYL-3,8,13,17-TETRAMETHYL-21H,23H-PORPHINE-2,18-DIPROPANOATO(4-)-.KAPPA.N21,.KAPPA.N22,.KAPPA.N23,.KAPPA.N24)-, HYDROGEN (1:2), (SP-4-2)-

Common Name

English

COBALT-HEME

Common Name

English

COBALTATE(2-), (7,12-DIETHENYL-3,8,13,17-TETRAMETHYL-21H,23H-PORPHINE-2,18-DIPROPANOATO(4-)-N21,N22,N23,N24)-, DIHYDROGEN, (SP-4-2)-

Common Name

English

COBALT(II) PROTOPORPHYRIN IX

Common Name

English

COBALT, (DIHYDROGEN PROTOPORPHYRIN IX-ATO(2-))-

Common Name

English

COBALT, (DIHYDROGEN 3,7,12,17-TETRAMETHYL-8,13-DIVINYL-2,18-PORPHINEDIPROPIONATO(2-))-

Common Name

English

COBALT PROTOPORPHYRIN [JAN]

Common Name

English

21H,23H-PORPHINE-2,18-DIPROPANOIC ACID, 7,12-DIETHENYL-3,8,13,17-TETRAMETHYL-, COBALT COMPLEX

Common Name

English

Code System Code Type Description

FDA UNII

63AAN3JDZE

Created by admin on Mon Mar 31 21:29:30 GMT 2025 , Edited by admin on Mon Mar 31 21:29:30 GMT 2025

PRIMARY

SMS_ID

300000023093

Created by admin on Mon Mar 31 21:29:30 GMT 2025 , Edited by admin on Mon Mar 31 21:29:30 GMT 2025

PRIMARY

CAS

14325-03-2

Created by admin on Mon Mar 31 21:29:30 GMT 2025 , Edited by admin on Mon Mar 31 21:29:30 GMT 2025

PRIMARY

NSC

267101

Created by admin on Mon Mar 31 21:29:30 GMT 2025 , Edited by admin on Mon Mar 31 21:29:30 GMT 2025

PRIMARY

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/26255181 | https://www.ncbi.nlm.nih.gov/pubmed/15059790 | https://www.ncbi.nlm.nih.gov/pubmed/24255720

CNS Activity

Approval Year

Targets

Conditions

Approved Use

Approved Use

Approved Use

Approved Use

Approved Use

Approved Use

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26255181 | https://www.ncbi.nlm.nih.gov/pubmed/15059790 | https://www.ncbi.nlm.nih.gov/pubmed/24255720