Compound Detail

CHEMBL1355736

THEOPHYLLINE

💊 Approved Drug

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💊 Approved Drug

Cn1c(=O)c2nc[nH]c2n(C)c1=O.O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL1355736
Name	THEOPHYLLINE
Phase	Approved
Structure Type	MOL
InChI Key	INQSMEFCAIHTJG-UHFFFAOYSA-N
Therapeutic	✓ Yes
Parent Compound	CHEMBL190
Active Moiety	CHEMBL190

Known Names

Accurbron Aerolate Aerolate iii Aerolate jr Aerolate sr Aquaphyllin Bronkodyl Duraphyl Elixicon Elixomin Elixophyllin Elixophyllin sr +18 more

Targets

258

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

180.2

MW (Da)

-1.04

ALogP

HBA

HBD

72.7

PSA (Å²)

0.56

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Protein
First Approval	1976
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral Parenteral

Extended Properties

Molecular Formula	C7H10N4O3
MW	198.18
Aromatic Rings	2
Heavy Atoms	13
NP-Likeness	-0.75

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Phosphodiesterase 4 inhibitor	INHIBITOR	Phosphodiesterase 4	✓	✓
Phosphodiesterase 3 inhibitor	INHIBITOR	Phosphodiesterase 3	✓	✓
Adenosine receptor antagonist	ANTAGONIST	Adenosine receptor	✓	✓

Indications

Asthma Bronchitis, Chronic Lung Diseases, Obstructive Pulmonary Disease, Chronic Obstructive Respiratory Insufficiency Altitude Sickness Apnea Hernias, Diaphragmatic, Congenital Kidney Diseases Leukemia Pseudohypoparathyroidism Pseudohypoparathyroidism Pseudohypoparathyroidism Renal Insufficiency, Chronic Severe Acute Respiratory Syndrome Virus Diseases Carcinoma, Non-Small-Cell Lung Depressive Disorder, Major Hypertension, Pulmonary Leukemia, Myeloid, Acute

ATC Classification

R03DA04

theophylline

Level 1: RESPIRATORY SYSTEM

Level 2: DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES

R03DA54

theophylline, combinations excl. psycholeptics

Level 1: RESPIRATORY SYSTEM

Level 2: DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES

R03DA74

theophylline, combinations with psycholeptics

Level 1: RESPIRATORY SYSTEM

Level 2: DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES

Activity Summary

Ki 190 meas. best 9.22

IC50 55 meas. best 6.03

Kd 8 meas. best 6.4

EC50 5 meas. best 4.55

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Adenosine receptor A2a CHEMBL251	Ki	9.22	5.3808	0.6	24
Adenosine receptor A1 CHEMBL226	Ki	9.22	5.3742	0.6	19
Adenosine receptor A3 CHEMBL256	Ki	7.85	4.495	14.0	20
Adenosine receptor CHEMBL2111386	Ki	6.82	5.38	150.0	6
No relevant target CHEMBL2362975	Kd	6.4	6.4	400.0	1
Adenosine receptor A1 CHEMBL318	Ki	6.16	4.9941	700.0	32
Unchecked CHEMBL612545	IC50	6.03	4.5375	940.0	4
Adenosine A2 receptor CHEMBL2094117	Ki	5.88	4.7956	1310.0	18
Adenosine receptor A2a CHEMBL251	Kd	5.79	5.5767	1642.3	3
Adenosine receptor A1 CHEMBL4975	IC50	5.61	5.255	2430.0	2
Adenosine receptor A2b CHEMBL255	Ki	5.57	5.0914	2700.0	14
Cavia porcellus CHEMBL369	IC50	5.52	5.056	3000.0	5
Adenosine receptor A1 CHEMBL4975	Ki	5.42	5.293	3800.0	10
Adenosine receptor A2a CHEMBL302	Ki	5.17	4.7691	6700.0	11
Adenosine receptor A1 CHEMBL2304404	Ki	5.01	4.7638	9800.0	8
Trachea CHEMBL4296541	IC50	4.94	4.94	11570.0	1
Adenosine receptor A2a CHEMBL251	IC50	4.92	4.92	12007.0	1
Adenosine receptor A1 CHEMBL226	Kd	4.92	4.92	12000.0	1
Adenosine receptor A2a CHEMBL2605	Ki	4.89	4.8425	13000.0	4
Adenosine A2 receptor CHEMBL2094257	Ki	4.86	4.835	13800.0	4
Adenosine receptor A2b CHEMBL2592	Ki	4.82	4.82	15100.0	3
Adenosine receptor A1 CHEMBL226	IC50	4.77	4.77	17104.0	1
Adenosine receptor A1 CHEMBL318	IC50	4.72	4.6567	19000.0	3
NON-PROTEIN TARGET CHEMBL3879801	IC50	4.7	4.7	19900.0	1
Unchecked CHEMBL612545	Ki	4.68	4.49	21000.0	3
Cavia porcellus CHEMBL369	EC50	4.55	4.55	28000.0	2
Adenosine receptor A2a CHEMBL251	EC50	4.55	4.55	28200.0	1
Cavia porcellus CHEMBL369	Kd	4.53	4.53	29512.1	1
Phosphodiesterase 4 CHEMBL2093863	IC50	4.3	4.195	50000.0	2
Phosphodiesterase 4 CHEMBL2093863	Ki	4.25	4.25	56800.0	2
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform CHEMBL3130	IC50	4.12	4.12	75000.0	1
Phosphodiesterase 3B CHEMBL5129	Ki	4.11	4.11	77000.0	1
Alkaline phosphatase, tissue-nonspecific isozyme CHEMBL5979	Ki	4.09	4.09	82000.0	1
Adenosine receptor A3 CHEMBL3360	Ki	4.07	4.035	85000.0	2
Transmembrane domain-containing protein TMIGD3 CHEMBL3712907	Ki	4.06	4.06	86400.0	1
Phosphodiesterase 3B CHEMBL5129	IC50	4.05	4.05	90000.0	1
Heart phosphodiesterase CHEMBL2111408	IC50	4.04	4.04	92000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	2.2	mL.min-1.kg-1	Rattus norvegicus
CL	1.5	mL.min-1.kg-1	Canis lupus familiaris
CL	0.6	mL.min-1.kg-1	Homo sapiens
CL	0.65	mL.min-1.kg-1	Homo sapiens
CL	0.86	mL.min-1.kg-1	Homo sapiens
CL	0.8	mL.min-1.kg-1	Homo sapiens
CL	0.86	mL.min-1.kg-1	Homo sapiens
CL	0.86	mL.min-1.kg-1	Homo sapiens
CL	4.79	mL.min-1.g-1	Homo sapiens
CL	5.75	uL.min-1.(10^6cells)-1	Rattus norvegicus
CL	3.0	uL.min-1.(10^6cells)-1	Homo sapiens
CL	2.6	mL.min-1.kg-1	Homo sapiens
CL	1.73	uL.min-1.(10^6cells)-1	Homo sapiens
CL	1.29	mL.min-1.kg-1	Homo sapiens
F	80.0	%	Homo sapiens
F	98.8	%	Homo sapiens
Fu	0.46	-	Homo sapiens
Fu	0.61	-	Homo sapiens
Fu	0.61	-	Homo sapiens
Fu	0.53	-	Not specified
Fu	0.989	-	Homo sapiens
MRT	9.9	hr	Homo sapiens
T1/2	7.2	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Adenosine receptor A1	Ki	=	0.6	nM	9.22	Binding affinity for adenosine A1 receptor by using as [3H]CPX iradioligand n me...	15664822
Adenosine receptor A2a	Ki	=	0.6	nM	9.22	Binding affinity for adenosine A2a receptor by using as [3H]ZM-241385 radioligan...	15664822
Adenosine receptor A3	Ki	=	14.0	nM	7.85	Binding affinity for adenosine A3 receptor by displacement of specific binding o...	15664822
Adenosine receptor	Ki	=	150.0	nM	6.82	Antagonist binding of 2-chloro-[3H]-adenosine to rat brain	6279840
No relevant target	Kd	=	400.0	nM	6.4	Dissociation constant of the compound	15293991
Adenosine receptor A1	Ki	=	700.0	nM	6.16	Inhibition of [3H]-CHA binding to rat brain membrane Adenosine A1 receptor	2258897
Unchecked	IC50	=	940.0	nM	6.03	Inhibition of Adenylate Cyclase in Rat adipocytes	2258897
Adenosine A2 receptor	Ki	=	1310.0	nM	5.88	Binding of Adenosine A2 receptor in whole rat brain membrane using [3H]CHA as a ...	2258897
Adenosine receptor A2a	Kd	=	1642.33	nM	5.79	The A2A-StaR2 receptor has been purified from membranes in n-decyl-beta-D-maltos...	-
Adenosine receptor A2a	Ki	=	1710.0	nM	5.77	Displacement of [3H]NECA from human A2A adenosine receptor expressed in CHO cell...	-
Adenosine receptor A2a	Ki	=	1700.0	nM	5.77	Displacement of [3H]CGS21680 from human adenosine A2A receptor expressed in HEK2...	23200243
Adenosine receptor A2a	Ki	=	1710.0	nM	5.77	Binding affinity to human adenosine A2A receptor by radioligand displacement ass...	30108984
Adenosine receptor A2a	Ki	=	1710.0	nM	5.77	Displacement of [3H]NECA from human adenosine receptor A2A expressed in CHO cell...	31738058
Adenosine receptor A2a	Ki	=	1710.0	nM	5.77	Displacement of [3H]MSX2 from human adenosine receptor A2A expressed in HEK293 c...	31780082
Adenosine receptor A2a	Ki	=	1710.0	nM	5.77	Antagonist activity at adenosine A2A receptor (unknown origin)	34695776
Adenosine receptor	Ki	=	2000.0	nM	5.7	Antagonist binding of L-N6-phenyl-isopropyl)-[3H]adenosine to rat brain	6279840
Adenosine receptor A2a	Ki	=	2030.0	nM	5.69	Competitive binding affinity to human adenosine A2A receptor expressed in HEK293...	23200243
Adenosine receptor A1	IC50	=	2430.0	nM	5.61	Binding affinity against bovine brain adenosine A1 receptor using N6-[3H]- cyclo...	2991519
Adenosine receptor A2b	Ki	=	2700.0	nM	5.57	Displacement of [3H]DPCPX from human recombinant adenosine A2B receptor expresse...	20202853
Cavia porcellus	IC50	=	3000.0	nM	5.52	Inhibition of 2-chloroadenosine-induced relaxation in histamine-contracted guine...	3361572

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885861	Rattus norvegicus	1388
-	10.6019/CHEMBL3885881	Rattus norvegicus	405
1501234	10.1021/jm00094a022	Rattus norvegicus	19
16472241	10.2174/1570163043334794	Hepatotoxicity	18
6161252	10.1021/jm00185a008	Rattus norvegicus	15
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
8355252	10.1021/jm00069a009	Mus musculus	11
28107736	10.1016/j.ejmech.2017.01.011	No relevant target	11
8355252	10.1021/jm00069a009	Rattus norvegicus	10
21661720	10.1021/jm2003798	Adenosine receptor A2a	9
17533133	10.1016/j.bmc.2007.05.025	Vibrio harveyi	8
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
20070106	10.1021/jm901371v	Homo sapiens	8
6279840	10.1021/jm00345a001	Adenosine receptor	7
6279842	10.1021/jm00345a010	Unchecked	6
24853321	10.1016/j.bmc.2014.04.053	B16-F0	6
-	10.6019/CHEMBL3301361	ADMET	6
24433966	10.1016/j.bmc.2013.12.062	B16-F10	6
6265635	10.1021/jm00138a002	Rattus norvegicus	6

Data from ChEMBL 36 via Core Engine